Phthalic acid diamide derivatives, fluorine-containing aniline compounds as starting material, agricultural and horticultural insecticides, and a method for application of the insecticides

ABSTRACT

The present invention provides a phthalic acid diamide derivative represented by the general formula (I)                    
     (wherein R 1 , R 2  and R 3  are each H, C 3 -C 6  cycloalkyl group, group of the formula —A 1 —Q l  or the like; X may be the same or different and are each halogen atom, nitro group, phenyl group, group of the formula —A 2 —R 7  or the like; n is 1 to 4; Y may be same or different and are each halogen atom, cyano group, phenyl group, group of the formula —A 2 —R 7  or the like; m is 1 to 5; Z 1  and Z 2  are each O or S), fluorine-containing aniline compound represented by the general formula (ST-I) as starting material for said phthalic acid diamide derivative                    
     (wherein R a  is halogen atom, C 1 -C 6  alkyl group or the like and R b , R c  and R d  is H or C 2 -C 6  perfluoroalkyl group), and an agricultural and horticultural insecticide containing said phthaldiamide derivative, as well as to provide a method for use of said insecticide. The agricultural and horticultural insecticides of the present invention show excellent activities for controlling injurious insects.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a division of Ser. No. 09/250,261, filed Feb. 16, 1999, now U.S. Pat. No. 6,362,369, which is a continuation-in-part application of earlier U.S. application Ser. No. 09/198,391 filed Nov. 24, 1998 now abandoned of which contents are all incorporated herein by reference.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to phthalic acid diamide derivatives, fluorine-containing aniline compounds as starting material for said derivative, agricultural and horticultural insecticides containing said derivative as an active ingredient, and a method for application of the insecticides.

2. Related Art

Japanese Patent Application Nos. 59-163353 and 61-180753 and J.C.S. Perkin I, 1338-1350, (1978), etc. disclose some of the phthalic acid diamide derivatives of the present invention but neither describe nor suggest their usefulness as agricultural and horticultural insecticides. JP-A-63-99046 and JP-A-6-184065 describe the fact that anilines similar to the fluorine-containing aniline compound of the present invention are useful as intermediates of benzoylurea type insecticides.

SUMMARY OF THE INVENTION

The present inventors earnestly studied in order to develop a novel agricultural and horticultural insecticide, and consequently found that the phthalic acid diamide derivatives represented by the general formula (I) of the present invention are novel compounds not known as agricultural and horticultural insecticides in any literature and that said derivatives including the compounds disclosed in the above references can be used for a new purpose as agricultural and horticultural insecticides. Further, the present inventors found that the fluorine-containing aniline compounds represented by the general formula (ST-I) of the present invention are novel compounds which have not been known in any literature and is useful as an intermediate of a medicine, agrochemical, chemical product etc. In particular, they found that the fluorine-containing aniline compound of the general formula (ST-I) is useful as a starting material for the agricultural and horticultural insecticide containing the phthalic acid diamide derivative of the general formula (I) as an active ingredient. Thus, the present invention has been accomplished.

DETAILED DESCRIPTION OF THE INVENTION

The present invention relates to phthalic acid diamide derivatives of the general formula (I),

wherein R¹, R² and R³ may be the same or different, and are each a hydrogen atom, a cyano group, a C₃-C₆ cycloalkyl group, a halo-C₃-C₆ cycloalkyl group, a C₃-C₆ cycloalkenyl group, a halo-C₃-C₆ cycloalkenyl group or a group of the formula —A¹Q_(l) (wherein A¹ is —O—, —S—, —SO₂—, —C(═O)—, a group of the formula —N(R⁴)— (wherein R⁴ is a C₁-C₆ alkylcarbonyl group, a halo-C₁-C₆ alkylcarbonyl group, a C₁-C₆ alkoxycarbonyl group, a phenylcarbonyl group, or a substituted phenylcarbonyl group having at least one substituent which may be the same or different, and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different), a C₁-C₈ alkylene group, a C₃-C₆ alkenylene group or a C₃-C₆ alkynylene group;

(1) when A¹ is —O— or a group of the formula —N(R⁴)— (wherein R⁴ is the same as defined above), then Q is a hydrogen atom, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₃-C₆ alkenyl group, a halo-C₃-C₆ alkenyl group, a C₃-C₆ alkynyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkyl sulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a phenyl-C₁-C₄ alkyl group or a substituted phenyl-C₁-C₄ alkyl group having at least one substituent, in the phenyl ring, which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different;

(2) when A¹ is —S—, —SO₂— or —C(═O)—, then Q is a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₃-C₆ alkenyl group, a halo-C₃-C₆ alkenyl group, a C₃-C₆ alkynyl group, a C₁-C₆ alkoxy group, a mono-C₁-C₆ alkylamino group, a di-C₁-C₆ alkylamino group which may be the same or different, a C₁-C₆ alkoxycarbonylamino group, a C₁-C₆ alkoxycarbonyl-C₁-C₆ alkylamino group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a phenylamino group, a substituted phenylamino group having at least one substituent, in the phenyl ring, which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which means pyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group or a pyrazolyl group), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different,

(3) when A¹ is a C₁-C₈ alkylene group, a C₃-C₆ alkenylene group or a C₃-C₆ alkynylene group, then Q is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a halo-C₁-C₆ alkyl group, a C₃-C₆ cycloalkyl group, a halo-C₃-C₆ cycloalkyl group, a C₁-C₆ alkoxycarbonyl group, a di-C₁-C₆ alkoxyphosphoryl group which may be the same or different, a di-C₁-C₆ alkoxythiophosphoryl group which may be the same or different, a diphenylphosphino group, a diphenylphosphono group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, or a group of the formula —Z³—R⁵ (wherein Z³ is —O—, —S—, —SO—, —SO²— or a group of the formula —N(R⁶)— (wherein R⁶ is a hydrogen atom, a C₁-C₆ alkylcarbonyl group, a halo-C₁-C₆ alkylcarbonyl group, a C₁-C₆ alkoxycarbonyl group, a phenylcarbonyl group, a substituted phenylcarbonyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a phenyl C₁-C₄ alkoxycarbonyl group, or a substituted phenyl C₁-C₄ alkoxycarbonyl group having at least one substituent, in the phenyl ring, which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different); and

R⁵ is a hydrogen atom, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₃-C₆ alkenyl group, a halo-C₃-C₆ alkenyl group, a C₃-C₆ alkynyl group, a halo-C₃-C₆ alkynyl group, a C₃-C₆ cycloalkyl group, a halo-C₃-C₆ cycloalkyl group, a C₁-C₆ alkylcarbonyl group, a halo C₁-C₆ alkylcarbonyl group, a C₁-C₆ alkoxycarbonyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a phenyl C₁-C₄ alkyl group, a substituted phenyl C₁-C₄ alkyl group having at least one substituent, in the phenyl ring, which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different);

l is an integer of 1 to 4); further,

R¹ and R² may form a 4 to 7 membered ring by combining to each other, in which the ring may contain the same or different 1 to 3 hetero atoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom;

X may be the same or different, and is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C₃-C₆ cycloalkyl group, a halo-C₃-C₆ cycloalkyl group, a phenyl group, a substituted phenyl group having at least one substituents which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined the above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, or a group of the formula —A²—R⁷ (wherein A² is —O—, —S—, —SO—, —SO₂—, —C(═O)—, —C(═NOR⁸)— (wherein R⁸ is a hydrogen atom, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₃-C₆ alkenyl group, a halo-C₃-C₆ alkenyl group, a C₃-C₆ alkynyl group, a C₃-C₆ cycloalkyl group, a phenyl-C₁-C₄ alkyl group, or a substituted phenyl-C₁-C₄ alkyl group having at least one substituent, in the phenyl ring, which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different), a C₁-C₆ alkylene group, a halo-C₁-C₆ alkylene group, a C₂-C₆ alkenylene group, a halo-C₂-C₆ alkenylene group, a C₂-C₆ alkynylene group or a halo-C₃-C₆ alkynylene group;

(1) when A² is —O—, —S—, —SO— or —SO₂—, then R⁷ is a hydrogen atom, a C₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₃-C₆ alkenyl group, a halo-C₃-C₆ alkenyl group, a C₃-C₆ alkynyl group, a halo-C₃-C₆ alkynyl group, a C₃-C₆ cycloalkyl group, a halo-C₃-C₆ cycloalkyl group, a C₃-C₆ cycloalkenyl group, a halo-C₃-C₆ cycloalkenyl group, a di-C₁-C₆ alkoxyphosphoryl group which may be the same or different, a di-C₁-C₆ alkoxythiophosphoryl group which may be the same or different, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituents which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, or a group of the formula —A³—R⁹ (wherein A³ is —C(═O)—, —SO₂—, a C₁-C₆ alkylene group, a halo-C₁-C₆ alkylene group, a C₂-C₆ alkenylene group, a halo-C₂-C₆ alkenylene group, a C₃-C₆ alkynylene group or a halo-C₃-C₆ alkynylene group,

(i) when A³ is —C(═O)— or —SO²—, then R⁹ is a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₁-C₆ alkoxy group, a mono-C₁-C₆ alkylamino group, a di-C₁-C₆ alkylamino group which may be the same or different, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined the above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different,

(ii) when A³ is a C₁-C₆ alkylene group, a halo-C₁-C₆ alkylene group, a C₂-C₆ alkenylene group, a halo-C₂-C₆ alkenylene group, a C₃-C₆ alkynylene group or a halo-C₃-C₆ alkynylene group, then R⁹ is a hydrogen atom, a halogen atom, a cyano group, a C₃-C₆ cycloalkyl group, a halo-C₃-C₆ cycloalkyl group, a C₁-C₆ alkoxycarbonyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, or a group of the formula —A⁴—R¹⁰ (wherein A⁴ is —O—, —S—, —SO—, —SO₂—, —C(═O)—, or a group of the formula —N(R¹¹)— (wherein R¹¹ is a hydrogen atom, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₃-C₆ alkenyl group, a C₃-C₆ alkynyl group, a C₃-C₆ cycloalkyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different); and

R¹⁰ is a hydrogen atom, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₃-C₆ alkenyl group, a halo-C₃-C₆ alkenyl group, a C₃-C₆ alkynyl group, a halo-C₃-C₆ alkynyl group, a C₃-C₆ cycloalkyl group, a halo-C₃-C₆ cycloalkyl group, a C₃-C₆ cycloalkenyl group, a halo-C₃-C₆ cycloalkenyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined the above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined the above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different));

(2) when A² is —C(═O)— or a group of the formula —C(═NOR⁸)— (wherein R⁸ is the same as defined above), then R⁷ is a C₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₃-C₆ cycloalkyl group, a halo-C₃-C₆ cycloalkyl group, a C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a mono-C₁-C₆ alkylamino group, a di-C₁-C₆ alkylamino group which may be the same or different, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a phenylamino group, a substituted phenylamino group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having one or more substituents which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different,

(3) when A² is a C₁-C₆ alkylene group, a halo-C₁-C₆ alkylene group, C₂-C₆ alkenylene group, a halo-C₂-C₆ alkenylene group, a C₂-C₆ alkynylene group or a halo-C₃-C₆ alkynylene group, then R⁷ is a hydrogen atom, a halogen atom, a C₃-C₆ cycloalkyl group, a halo-C₃-C₆ cycloalkyl group, a C₁-C₆ alkoxycarbonyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, or a group of the formula —A⁵—R¹² (wherein A⁵ is —O—, —S—, —SO—, —SO₂— or a group of the formula —N(R¹³)— (wherein R¹³ is a hydrogen atom, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a C₃-C₆ cycloalkyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituents which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different); and R¹² is a hydrogen atom, a C₃-C₆ cycloalkyl group, a halo-C₃-C₆ cycloalkyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituents which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, or a group of the formula —A⁶—R¹⁴ (wherein A is —C(═O)—, —SO₂—, a C₁-C₆ alkylene group, a halo-C₁-C₆ alkylene group, a C₂-C₆ alkenylene group, a halo-C₂-C₆ alkenylene group, a C₂-C₆ alkynylene group or a halo-C₃-C₆ alkynylene group;

(i) when A⁶ is —C(═O)— or —SO₂—, then R¹⁴ is a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected.from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined the above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different;

(ii) when A⁶ is a C₁-C₆ alkylene group, a halo-C₁-C₆ alkylene group, a C₂-C₆ alkenylene group, a halo-C₂-C₆ alkenylene group, a C₂-C₆ alkynylene group or a halo-C₃-C₆ alkynylene group, then R¹⁴ is a hydrogen atom, a halogen atom, a cyano group, a C₃-C₆ cycloalkyl group, a halo-C₃-C₆ cycloalkyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a C₁-C₆ alkylcarbonyl group, a halo-C₁-C₆ alkylcarbonyl group, a C₁-C₆ alkoxycarbonyl group, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and are selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a phenoxy group, a substituted phenoxy group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a phenylthio group, a substituted phenylthio group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆-alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined.above), or a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different)));

n is an integer of 1 to 4;

further, X may form a condensed ring (which means naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, chroman, isochroman, indole, indoline, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole, benzimidazole or indazole), by combining together with the adjacent carbon atoms in the phenyl ring, and said condensed ring may have at least one substituents, which may be the same or different, and selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group, a di-C₁-C₆ alkylamino group which may be the same or different, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined above), and a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different;

Y is the same or different, and is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C₃-C₆ cycloalkyl group, a halo-C₃-C₆ cycloalkyl group, a di-C₁-C₆ alkoxyphosphoryl group which may be the same or different, a di-C₁-C₆ alkoxythiophosphoryl group which may be the same or different, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined the above), a substituted heterocyclic group (wherein the heterocyclic group is the same as defined above) having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, or a group of the formula —A²—R⁷ (wherein A² and R⁷ are the same as defined above);

m is an integer of 1 to 5;

further, Y may form a condensed ring (the condensed ring is the same as defined above), by combining together with the adjacent carbon atoms in the phenyl ring, said condensed ring may have at least one substituents, which may be the same or different, and selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group, a di-C₁-C₆ alkylamino group which may be the same or different, a phenyl group, a substituted phenyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a naphthyl group, a substituted naphthyl group having at least one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different, a heterocyclic group (which is the same as defined above), and a substituted heterocyclic group (wherein said heterocyclic group is the same as defined above) having at lease one substituent which may be the same or different and is selected from the group consisting of a halogen atom, a cyano group, a nitro group, a C₁-C₆ alkyl group, a halo-C₁-C₆ alkyl group, a C₂-C₆ alkenyl group, a halo-C₂-C₆ alkenyl group, a C₂-C₆ alkynyl group, a halo-C₂-C₆ alkynyl group, a C₁-C₆ alkoxy group, a halo-C₁-C₆ alkoxy group, a C₁-C₆ alkylthio group, a halo-C₁-C₆ alkylthio group, a C₁-C₆ alkylsulfinyl group, a halo-C₁-C₆ alkylsulfinyl group, a C₁-C₆ alkylsulfonyl group, a halo-C₁-C₆ alkylsulfonyl group, a mono-C₁-C₆ alkylamino group and a di-C₁-C₆ alkylamino group which may be the same or different;

Z¹ and Z² are each represents an oxygen atom or a sulfur atom; provided that,

(1) when X, R¹ and R³ are hydrogen atoms at the same time; m is an integer of 2; Y at 2-position is a fluorine atom and Y at 3-position is a chlorine atom; then R² is not ethyl group, isopropyl group, cyclohexyl group, 2-propenyl group, methylthiopropyl group and α-methylbenzyl group,

(2) when X and R³ are hydrogen atoms at the same time; m is an integer of 2; Y at 2-position is a fluorine atom and Y at 3-position is a chlorine atom; then the 4 to 7 membered ring by combining R¹ and R² to each other, in which the ring may contain the same or different 1 to 3 hetero atoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom is not morpholino group,

(3) when X, R¹ and R³ are hydrogen atoms at the same time; and R² is 1,2,2-trimethylpropyl group; then Y is not a hydrogen atom,

(4) when X, R¹ and R³ are hydrogen atoms at the same time; R² is 2,2-dimethylpropyl group; and m is an integer of 1; then Y is not 2-ethoxy group, and

(5) when X, R¹ and R³ are hydrogen atoms at the same time; and R² is tert-butyl group group; and m is an integer of 1; then Y is not 4-chlorine atom, 2-nitro group, 4-nitro group, 3-methoxy group, 4-methoxy group and 2,6-dimethyl groups;

fluorine-containing aniline compounds represented by the general formula (ST-I) as starting material for the phthalic acid diamide derivatives:

(wherein R^(a) is a halogen atom, a C₁-C₆ alkyl group, a C₁-C₆ alkoxy group or a trifluoromethyl group, and each of R^(b), R^(c) and R^(d) is a hydrogen atom or a C₂-C₆ perfluoroalkyl group, provided that at least one of R^(b), R^(c) and R^(d) is not a hydrogen atom and that R^(c) is neither a pentafluoroethyl group nor a n-heptafluoropropyl group when R^(a) is a fluorine atom and each of R^(b) and R^(d) is a hydrogen atom); agricultural and horticultural insecticides containing as an active ingredient any of the phthalic acid diamide derivatives of the general formula (I) including known compounds; and a method for application of the insecticides.

In the definition of the general formula (I) representing the phthalic acid diamide derivative of the present invention, the halogen atom includes chlorine atom, bromine atom, iodine atom and fluorine atom. The term “C₁-C₆ alkyl” means a linear or branched alkyl group of 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl, or the like. The term “C₁-C₈ alkylene” means a linear or branched alkylene group of 1 to 8 carbon atoms, such as methylene, ethylene, propylene, trimethylene, dimethylmethylene, tetramethylene, i-butylene, dimethylethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene or the like. The term “halo-C₁-C₆ alkyl” means a substituted and linear or branched alkyl group of 1 to 6 carbon atoms having as the substituent(s) one or more halogen atoms which may be the same or different.

As the ring which R¹ and R² form by combining to each other, i.e., the 4- to 7-membered ring by combining to each other, in which the ring may contain the same or different 1 to 3 hetero atoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, there can be exemplified azetidine ring, pyrrolidine ring, pyrroline ring, piperidine ring, imidazolidine ring, imidazoline ring, oxazolidine ring, thiazolidine ring, isoxazolidine ring, isothiazolidine ring, tetrahydropyridine ring, piperazine ring, morpholine ring, thiomorpholine ring, dioxazine ring, dithiazine ring, etc.

The phthalic acid diamide derivative of the general formula (I) of the present invention contains an asymmetric carbon atom or some asymmetric center in the structural formula in some cases or has two optical isomers in some cases. The present invention includes these optical isomers and all mixtures containing the optical isomers in arbitrary proportions.

Preferable examples of each substituent of the phthalic acid diamide derivative of the general formula (I) of the present invention are as follows. Preferable examples of each of R¹ and R² which may be the same or different are hydrogen atom, C₁-C₆ alkyl groups such as methyl, ethyl, i-propyl, etc. Preferable examples of R³ are hydrogen atom, and C₁-C₆ alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, etc. Preferable examples of X are halogen atoms, nitro group, halo-C₁-C₆ alkyl groups, halo-C₁-C₆ alkoxy groups, halo-C₁-C₆ alkylthio groups, etc. Preferable examples of Y are halo-C₁-C₆ alkyl groups, halo-C₁-C₆ alkoxy groups, halo-C₁-C₆ alkylthio groups, etc.

The phthalic acid diamide derivative of the general formula (I) of the present invention can be produced, for example, by any of the processes illustrated below.

wherein R¹, R², X, n, Y and m are as defined above.

A phthalic anhydride derivative of the general formula (v) is reacted with an aniline of the general formula (IV) in the presence of an inert solvent to obtain a phthalimide derivative of the general formula (III). The phthalimide derivative (III) is reacted with an amine of the general formula (II) after or without being isolated, whereby a phthalic acid diamide derivative of the general formula (I-1) can be produced.

(1) General Formula (V)→General Formula (III)

As the inert solvent used in this reaction, any solvent may be used so long as it does not markedly inhibit the progress of the reaction. There can be exemplified aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc., chlorinated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; a cyclic or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, etc., esters such as ethyl acetate, etc.; amides such as dimethylformamide, dimethylacetamide, etc.; acids such as acetic acid, etc.; dimethyl sulfoxide; and 1,3-dimethyl-2-imidazolidinone. These inert solvents may be used alone or as a mixture thereof.

Since the reaction is an equimolar reaction, it is sufficient that the reactants are used in equimolar amounts, though either of them may be used in excess. If necessary, the reaction may be carried out under dehydrating conditions.

As to the reaction temperature, the reaction can be carried out in a temperature range of room temperature to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it may be properly chosen in a range of several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced. The desired compound can be subjected to the subsequent reaction without isolation from the reaction solution.

The phthalic anhydride derivative of the general formula (V) can be produced by the process described in J. Org. Chem., 52, 129 (1987), J. Am. Chem. Soc., 51, 1865 (1929), J. Am. Chem. Soc., 63, 1542 (1941), etc. The aniline of the general formula (IV) can be produced by the process described in J. Org. Chem., 29, 1 (1964), Angew. Chem. Int. Ed. Engl., 24, 871 (1985), Synthesis, 1984, 667, Bulletin of the Chemical Society of Japan, 1973, 2351, DE-2606982, JP-A-1-90163, etc.

(2) General Formula (III)→General Formula (I-1)

In this reaction, there can be used the inert solvents exemplified above as the inert solvent used in the reaction (1).

Since the reaction is an equimolar reaction, it is sufficient that the reactants are used in equimolar amounts, though the amine of the general formula (II) may be used in excess.

As to the reaction temperature, the reaction can be carried out in a temperature range of room temperature to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it may be properly chosen in a range of several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced.

wherein R¹, R², n, X, Y and m are as defined above, and X′ is a halogen atom or a nitro group, provided that X is other than a hydrogen atom or a nitro group.

A phthalimide derivative of the general formula (III-1) is reacted with a reactant corresponding to X in the presence of an inert solvent to obtain a phthalimide derivative of the general formula (III). The phthalimide derivative (III) is reacted with an amine of the general formula (II) after or without.being isolated, whereby a phthalic acid diamide derivative of the general formula (I-1) can be produced.

(1) General Formula (III-1)→General Formula (III)

This reaction can be carried out according to the methods described in J. Org. Chem., 42, 3415 (1977), Tetrahedron, 25, 5921 (1969), Synthesis, 1984, 667, Chem. Lett., 1973, 471, J. Org. Chem., 39, 3318 (1974), J. Org. Chem., 39, 3327 (1974), etc.

(2) General Formula (III)→General Formula (I-1)

This reaction can be carried out according to production process 1-(2).

wherein R¹, R², X, Y, m and n are as defined above.

A phthalic anhydride of the general formula (V-1) is reacted with an aniline of the general formula (IV) in the presence of an inert solvent to obtain a phthalimide derivative of the general formula (III-2). The phthalimide derivative (III-2) is subjected to catalytic reduction with hydrogen after or without isolation to obtain a phthalimide derivative of the general formula (III-3). The phthalimide derivative (III-3) is converted to a phthalimide derivative of the general formula (III) by adding a diazotizing agent and then a metal salt after or without isolation of the phthalimide derivative (III-3). The phthalimide derivative (III) is reacted with an amine of the general formula (II) after or without being isolated, whereby a phthalic acid diamide derivative of the general formula (I-1) can be produced.

(1) General Formula (V-1)→General Formula (III-2)

The desired compound can be produced by this reaction in the same manner as in production process 1-(1).

(2) General Formula (III-2)→General Formula (III-3)

Any solvent may be used in this reaction so long as it does not markedly inhibit the progress of the reaction. There can be exemplified alcohols such as methanol, ethanol, propanol, etc.; acyclic or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, etc., and acids such as acetic acid, etc. These inert solvents may be used alone or as a mixture thereof.

As the catalyst for catalytic reduction used in this reaction, there can be exemplified palladium carbon, Raney nickel, palladium black, platinum black, etc. The amount of the catalyst used may be properly chosen in a range of 0.1 to 10% by weight based on the weight of the phthalimide derivative of the general formula (III-2). This reaction is carried out under a hydrogen atmosphere and the hydrogen pressure may be properly chosen in a range of 1 to 10 atmospheric pressure.

As to the reaction temperature, the reaction can be carried out in a temperature range of room temperature to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it may be properly chosen in a range of several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated from the reaction mixture containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced. The desired compound can be subjected to the subsequent reaction without isolation from the reaction mixture.

(3) General Formula (III-3)→General Formula (III)

In this reaction, an acidic solvent can be used as an inert solvent. The acidic solvent includes, for example, an aqueous hydrochloric acid solution, an aqueous hydrobromic acid solution, an aqueous hydroiodic acid solution, an aqueous sulfuric acid solution, acetic acid and trifluoroacetic acid. These acidic solvents may be used alone or as a mixture thereof. In addition, these acidic solvents may be used in admixture with ethers such as tetrahydrofuran, dioxane, etc.

The diazotizing agent includes, for example, sodium nitrite, nitrosyl hydrogensulfate and alkyl nitrites. The amount of the diazotizing agent used may be properly chosen in a range of equal amount to excess amount relative to the amount of the phthalimide derivative of the general formula (III-3).

As to the reaction temperature, the reaction can be carried out in a temperature range of −50° C. to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it may be properly chosen in a range of several minutes to 48 hours.

As the metal salt added after the production of a diazonium salt, there can be used, for example, cuprous chloride, cuprous bromide, potassium iodide, copper cyanide, potassium xanthate and sodium thiorate. The amount of the metal salt used may be properly chosen in a range of 1 equivalent to excess equivalents per equivalent of the phthalimide derivative of the general formula (III-3).

After completion of the reaction, the desired compound is isolated from the reaction mixture containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced. The desired compound can be subjected to the subsequent reaction without isolation from the reaction mixture.

The reaction can be carried out according to the method described in Org. Synth., IV, 160 (1963), Org. Synth., III, 809 (1959), J. Am. Chem. Soc., 92, 3520 (1970), etc.

(4) General Formula (III)→General Formula (I-1)

The desired compound can be produced by this reaction in the same manner as in production process 1-(2).

wherein R¹, R², X, Y, in and n are as defined above.

A phthalimide derivative of the general formula (III-2) is reacted with an amine of the general formula (II) in the presence of an inert solvent to obtain a phthalic acid diamide derivative of the general formula (I-3). The phthalic acid diamide derivative (I-3) is subjected to catalytic reduction with hydrogen after or without isolation to obtain a phthalic acid diamide derivative of the general formula (I-2). A phthalic acid diamide derivative of the general formula (I-1) can be produced from the phthalic acid diamide derivative (I-2) by adding a diazotizing agent and then a metal salt after or without isolating the phthalic acid diamide derivative (I-2).

(1) General Formula (III-2)→General Formula (I-3)

The desired compound can be produced by this reaction in the same manner as in production process 1-(2).

(2) General Formula (I-3)→General Formula (I-2)

The desired compound can be produced by this reaction in the same manner as in production process 3-(2).

(3) General Formula (I-2)→General Formula (I-1)

The desired compound can be produced by this reaction in the same manner as in production process 3-(3).

wherein R¹, R², R³, X, n, Y and m are as defined above.

A phthalic anhydride derivative of the general formula (V) is reacted with an amine of the general formula (II) in the presence of an inert solvent to obtain a phthalamide of the general formula (III-4). The phthalamide (III-4) is treated as follows after or without isolation. When R² of the phthalamide (III-4) is a hydrogen atom, the phthalamide (III-4) is condensed into a compound of the general formula (VI) in the presence of a condensing agent, and the compound (VI) is reacted with an aniline of the general formula (IV) in the presence of an inert solvent after or without being isolated. When R² of the phthalamide (III-4) is other than a hydrogen atom, the phthalamide (III-4) is condensed with an aniline of the general formula (IV) in the presence of a condensing agent. Thus, a phthalic acid diamide derivative of the general formula (I) can be produced.

Alternatively, a phthalic anhydride derivative of the general formula (V) is reacted with an aniline of the general formula (IV) in the presence of an inert solvent to obtain a phthalanilide of the general formula (III-5). The phthalanilide (III-5) is treated as follows after or without isolation. When R³ of the phthalanilide (III-5) is a hydrogen atom, the phthalanilide (III-5) is condensed into a compound of the general formula (VI-1) in the presence of a condensing agent, and the compound (VI-1) is reacted with an amine of the general formula (II) in the presence of an inert solvent after or without being isolated. When R³ of the phthalanilide (III-5) is other than a hydrogen atom, the phthalanilide (III-5) is condensed with an amine of the general formula (II) in the presence of a condensing agent. Thus, a phthalic acid diamide derivative of the general formula (I) can be produced.

(1) General Formula (V) or General Formula (VI-1)→General Formula (III-4) or General Formula (I), Respectively

The desired compound can be produced by this reaction in the same manner as in production process 1-(2).

(2) General Formula (III-4) or General Formula (III-5)→General Formula (VI) or General Formula (VI-1), Respectively

The desired compound can be produced by this reaction according to the method described in J. Med. Chem., 10, 982 (1967).

(3) General Formula (VI) or General Formula (V)→General Formula (I) or General Formula (III-5), Respectively

The desired compound can be produced by this reaction in the same manner as in production process 1-(2).

(4) General Formula (III-4) or General Formula (III-5)→General Formula (I)

The desired compound can be produced by reacting the phthalamide derivative of the general formula (III-4) or the general formula (III-5) with the aniline of the general formula (IV) or the amine of the general formula (II), respectively, in the presence of a condensing agent and an inert solvent. If necessary, the reaction can be carried out in the presence of a base.

The inert solvent used in the reaction includes, for example, tetrahydrofuran, diethyl ether, dioxane, chloroform and dichloromethane. As the condensing agent used in the reaction, any condensing agent may be used so long as it is used in usual amide synthesis. The condensing agent includes, for example, Mukaiyama reagent (e.g. 2-chloro-N-methylpyridinium iodide), 1,3-dicyclohexylcarbodiimide (DCC), carbonyldiimidazole (CDI) and diethyl phosphorocyanidate (DEPC). The amount of the condensing agent used may be properly chosen in a range of 1 mole to excess moles per mole of the phthalamide derivative of the general formula (III-4) or the general formula (III-5).

As the base usable in the reaction, there can be exemplified organic bases such as triethylamine, pyridine, etc. and inorganic bases such as potassium carbonate, etc. The amount of the base used may be properly chosen in a range of 1 mole to excess moles per mole of the phthalamide derivative of the general formula (III-4) or the general formula (III-5).

As to the reaction temperature, the reaction can be carried out in a temperature range of 0° C. to the boiling point of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it ranges from several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced.

wherein R¹, R², X, n, Y and m are as defined above, Hal is a halogen atom, and R¹⁵ is a (C₁-C₃)alkyl group.

A phthalic acid ester derivative of the general formula (VII) is halogenated into a phthaloyl halide of the general formula (VII-1) in the presence or absence of an inert solvent. The phthaloyl halide (VII-1) is reacted with an aniline of the general formula (IV) in the presence of an inert solvent and a base after or without being isolated, to obtain a phthalanilide of the general formula (III-6). The phthalanilide (III-6) is hydrolyzed into a phthalanilide of the general formula (III-5) in the presence or absence of an inert solvent after or without being isolated. The phthalanilide (III-5) is condensed into a phthalic anhydride derivative of the general formula (VI-1) after or without being isolated. The phthalic anhydride derivative (VI-1) is reacted with an amine of the general formula (II), whereby a phthalic acid diamide derivative of the general formula (I-1) can be produced.

(1) General Formula (VII)→General Formula (VII-1)

As the inert solvent usable in this reaction, any solvent may be used so long as it does not markedly inhibit the progress of the reaction. There can be exemplified aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc., chlorinated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, etc.; acyclic or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, etc., and esters such as ethyl acetate, etc. These inert solvents may be used alone or as a mixture thereof.

As the halogenating agents, there can be used, for example, thionyl chloride, phosphoryl chloride, and phosphorus trichloride. The amount of the halogenating agent used may be properly chosen in a range of 1 to 10 equivalents per equivalent of the phthalic acid ester of the general formula (VII).

As to the reaction temperature, the reaction can be carried out in a temperature range of 0° C. to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it may be properly chosen in a range of several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced. The desired compound can be subjected to the subsequent reaction without isolation from the reaction solution.

The phthalic acid ester of the general formula (VII) can be produced, for example, by the process described in J. Med. Chem., 31, 1466 (1988).

(2) General Formula (VII-1)→General Formula (III-6)

As the inert solvent used in this reaction, there may be used, for example, the inert solvents exemplified in production process 1-(1).

As the base, an inorganic base or an organic base may be used. As the inorganic base, there may be used, for example, hydroxides of alkali metals, such as sodium hydroxide, potassium hydroxide, etc. As the organic base, there may be used triethylamine, pyridine, etc. The amount of the base used may be properly chosen in a range of 0.5 to 3 equivalents per equivalent of the phthaloyl halide of the general formula (VII-1).

Since the reaction is an equimolar reaction, it is sufficient that the reactants are used in equimolar amounts, though the amount of the aniline of the general formula (IV) used may be properly chosen in a range of 0.5 to 2 equivalents per equivalent of the phthaloyl halide of the general formula (VII-1).

As to the reaction temperature, the reaction can be carried out in a temperature range of 0° C. to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it may be properly chosen in a range of several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced. The desired compound can be subjected to the subsequent reaction without isolation from the reaction solution.

(3) General Formula (III-6)→General Formula (III-5)

As the inert solvent usable in this reaction, there may be used water, alcohols (e.g. methanol, ethanol and propanol) as water-soluble solvents, and mixed solvents of water and a water-soluble solvent.

As the base used for the hydrolysis, there may be used, for example, hydroxides of alkali metals, such as sodium hydroxide, potassium hydroxide, etc. The amount of the base used may be properly chosen in a range of 1 to 10 equivalents per equivalent of the phthalanilide of the general formula (III-6).

As to the reaction temperature, the reaction can be carried out in a temperature range of 0° C. to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it may be properly chosen in a range of several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be produced. The desired compound can be subjected to the subsequent reaction without isolation from the reaction solution.

(4) General Formula (III-5)→General Formula (VI-1)

The desired compound can be produced by this reaction according to production process 5-(2).

(5) General Formula (VI-1)→General Formula (I-1)

The desired compound can be produced by this reaction according to production process 1-(2).

wherein R¹, R², R³, X, Y, m, n, Z¹ and Z² are as defined above.

A benzamide derivative of the general formula (VIII-1) or the general formula (VIII-2) or a thiobenzamide derivative of the general formula (VIII-3) or the general formula (VIII-4) obtained by thiocarbonylation of the benzamide derivative of the general formula (VIII-1) or the general formula (VIII-2), respectively, is subjected to ortho-metallation by using a metal reagent such as butyllithium. The compound thus obtained is directly reacted with an isocyanate or isothiocyanate derivative of the general formula (IX-1) or (IX-2), or the compound is reacted with carbon dioxide to obtain a phthalamide derivative of the general formula (III-4′) or the general formula (III-5′), which is treated in the same manner as in production processes 5-(1) to 5-(4). Thus, a phthalic acid diamide derivative of the general formula (I) can be produced.

(1) General Formula (VIII-1) or General Formula (VIII-2)→General Formula (VIII-3) or General Formula (VIII-4), Respectively

The desired compound can be produced by this reaction according to the method described in J. Org. Chem., 46, 3558 (1981).

(2) General Formula (VIII-1), General Formula (VIII-2), General Formula (VIII-3) or General Formula (VIII-4)→General Formula (I)

In this step, the benzamide derivative of the general formula (VIII-1) or the general formula (VIII-2) or the thiobenzamide derivative of the general formula (VIII-3) or the general formula (VIII-4) obtained by thiocarbonylation of the benzamide derivative of the general formula (VIII-1) or the general formula (VIII-2), respectively, is subjected to ortho-lithiation according to the method described in J. Org. Chem., 29, 853 (1964). The compound thus obtained is reacted with the isocyanate or isothiocyanate derivative of the general formula (IX-1) or (IX-2) at −80° C. to room temperature, whereby the desired compound can be produced.

After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be obtained.

(3) General Formula (VIII-1), General Formula (VIII-2), General Formula (VIII-3) or General Formula (VIII-4)→General Formula (III-4′) or the General Formula (III-5′)

In this step, the desired compound can be produced by carrying out the same ortho-lithiation as in the above step (2) and introducing carbon dioxide into the ortho-lithiation product at −80° C. to room temperature.

After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromatography, etc., whereby the desired compound can be obtained.

(4) General Formula (III-4′) or General Formula (III-5′)→General Formula (I)

In this step, the desired compound can be produced in the same manner as in production process 1-(2) or 5-(4).

Tables 1 and 2 show typical examples of the phthalic acid diamide derivative of the general formula (I) used as the active ingredient of the agricultural and horticultural insecticide of the present invention, but the examples are not intended in any way to limit the scope of the present invention.

General Formula (I):

TABLE 1 (Z¹, Z² = O) Physical Properties (melting No R¹ R² R³ Xn Ym point: ° C. 1 H H H 3-NO₂ 2-CH₃-5-Cl 173-175 2 CH₃ H H H 4-CF₃ 129-131 3 CH₃ H H 3-NO₂ 2-CH₃-5-Cl 169-171 4 CH₃ H H 3-NO₂ 2-CH₃-4-OCHF₂ 167-169 5 CH₃ CH₃ H 6-NO₂ 2-CH₃-5-Cl 171-173 6 CH₃ CH₃ H 6-NO₂ 2-CH₃-4-OCHF₂ 167-169 7 C₂H₅ H H H 4-CF₃ 134-136 8 C₂H₅ H H 3-Cl 2-CH₃-4-OCHF₂ 179-180 9 C₂H₅ H H 6-Cl 2-CH₃-4-OCHF₂ 189-190 10 C₂H₅ H H 3-NO₂ 2-CH₃-5-Cl 175-177 11 C₂H₅ H H 3-NO₂ 2-CH₃-4-OCHF₂ 207-208 12 C₂H₅ C₂H₅ H H 4-CF₃ 148-150 13 C₂H₅ C₂H₅ H 3-NO₂ 2-CH₃-5-Cl 175-177 14 n-C₃H₇ H H H 4-CF₃ 138-140 15 n-C₃H₇ H H 3-Cl 2-CH₃-4-OCHF₂ 171-173 16 n-C₃H₇ H H 6-Cl 2-CH₃-4-OCHF₂ 189-191 17 n-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCHF₂ 184-186 18 n-C₃H₇ H H 3-NO₂ 2-CH₃-5-Cl 187-189 19 n-C₃H₇ H H 5-CF₃ 2,6-(C₂H₅)2 230-232 20 i-C₃H₇ H H H H 192-194 21 i-C₃H₇ H H H 2-NO₂ 198-200 22 i-C₃H₇ H H H 4-NO₂ 139-141 23 i-C₃H₇ H H H 4-F 199-201 24 i-C₃H₇ H H H 2-CH₃ 191-193 Z5 i-C₃H₇ H H H 4-CF₃ 198-200 26 i-C₃H₇ H H H 3-CF₃ 174-176 27 i-C₃H₇ H H H 4-CF₂CF₂CF₃ 237-238 28 i-C₃H₇ H H H 4-(CF₂)₃CF₃ 137-139 29 i-C₃H₇ H H H 4-OCF₃ 155-157 30 i-C₃H₇ H H H 4-OCF₂CHFOC₃F₇-n 220-222 31 i-C₃H₇ H H H 3-SCF₃ 176-178 32 i-C₃H₇ H H H 4-SCHF₂ 169-170 33 i-C₃H₇ H H H 4-SCH₂CF₃ 166-167 34 i-C₃H₇ H H H 4-SCF₂CHF₂ 169-170 35 i-C₃H₇ H H H 4-S(CF₂)₃CF₃ 159-161 36 i-C₃H₇ H H H 4-SCF(CF₃)₂ 145-147 37 i-C₃H₇ H H H 4-SCF₂CBrF₂ 158-160 38 i-C₃H₇ H H H 4-SOCF₂CBrF₂ 180-182 39 i-C₃H₇ H H H 4-SO(CF₂)₃CF₃ 192-193 40 i-C₃H₇ H H H 4-SO₂CH₂CF₃ 169-170 41 i-C₃H₇ H H H 2,3-Cl₂ 151-153 42 i-C₃H₇ H H H 2,4-Cl₂ 162-164 43 i-C₃H₇ H H H 3,4-F₂ 172-174 44 i-C₃H₇ H H H 2,4-(CH₃)₂ 162-163 45 i-C₃H₇ H H H 2-Cl-4-CF₃ 197-199 46 i-C₃H₇ H H H 2-Cl-4-CF(CF₃)₂ 201-202 47 i-C₃H₇ H H H 2-Cl-4-OCF₃ 151-153 48 i-C₃H₇ H H H 2-Br-4-OCF₃ 146-147 49 i-C₃H₇ H H H 2-CH₃-3-Cl 196-198 50 i-C₃H₇ H H H 2-CH₃-4-Cl 180-182 51 i-C₃H₇ H H H 2-CH₃-5-Cl 161-162 52 i-C₃H₇ H H H 2-CH₃-4-Br 159-261 53 i-C₃H₇ H H H 2-CH₃-5-F 168-170 54 i-C₃H₇ H H H 2-CH₃-5-C₄H₉-t 203-204 55 i-C₃H₇ H H H 2-CH₃-4-CF₂CF₃ 157-159 56 i-C₃H₇ H H H 2-CH₃-4-CF₂CF₂CF₃ 177-178 57 i-C₃H₇ H H H 2-CH₃-4-CF(CF₃)₂ 230-231 58 i-C₃H₇ H H H 2-CH₃-4-OCHF₂ 135-137 59 i-C₃H₇ H H H 2-CH₃-4-OCF₃ 172-173 60 i-C₃H₇ H H H 2-CH₃-4-OCF₂CHF₂ 145-146 61 i-C₃H₇ H H H 2-CH₃-3-OCF₂CHClF 172-174 62 i-C₃H₇ H H H 2-CH₃-4-OCF₂CHClF 142-144 63 i-C₃H₇ H H H 2-CH₃-4-CF₂CBrF₂ 164-166 64 i-C₃H₇ H H H 2-CH₃-4-CF₂CCl₂F 172-173 65 i-C₃H₇ H H H 2-CH₃-4-OCF₂CHFCF₃ 151-152 66 i-C₃H₇ H H H 2-CH₃-4-OCF₂CBrFCF₃ 163-164 67 i-C₃H₇ H H H 2-CH₃-4-OCF₂CHFOCF₃ 146-148 68 i-C₃H₇ H H H 2-CH₃-4-SC₃H₇-i 178-180 69 i-C₃H₇ H H H 2-CH₃-4-OCH₂OCH₃ 165-166 70 i-C₃H₇ H H H 2-CH₃-4-OCH₂SCH₃ 160-162 71 i-C₃H₇ H H H 2-CH₃-4-COOCH₃ 163-165 72 i-C₃H₇ H H H 2-CH₃-4-OCH₂COOCH₃ 121-122 73 i-C₃H₇ H H H 2-CH₃-4-(F₅—PhO) 185-187 74 i-C₃H₇ H H H 2-CH₃-4-(3-CF₃—PhO) 150-152 75 i-C₃H₇ H H H 2-CH₃-4-(2-Cl-4-CF₃—PhO) 183-185 76 i-C₃H₇ H H H 2-CH₃-4-(4-Cl—Ph—CH₂O) 188-189 77 i-C₃H₇ H H H 2-CH₃-4-(4-Cl—PhS) 181-182 78 i-C₃H₇ H H H 2-CH₃-4-(5-CF₃-2-Pyi-O) 165-167 79 i-C₃H₇ H H H 2-CH₃-4-(3-Cl- 184-185 5-CF₃-2-Pyi-O) 80 i-C₃H₇ H H H 4-(3-Cl-5-CF₃-2-Pyi-S) 173-175 81 i-C₃H₇ H H H 2-CH₃-4-P═O(OC₂H₅)₂ 134-136 82 i-C₃H₇ H H H 2-CH₃-4-OP═S(OCH₃)₂ 132-134 83 i-C₃H₇ H H H 2-CF₃-4-OCHF₂ 147-149 84 i-C₃H₇ H H H 3,5-Cl₂-4-OCHF₂ 183-185 85 i-C₃H₇ H H H 3-N═C(CF₃)—NH-4 217-218 86 i-C₃H₇ H H H 3-N═C(CF₃)—N(CH₃)-4 171-173 87 i-C₃H₇ H H 3-Cl 4-C₄H₉-n 169-171 88 i-C₃H₇ H H 3-Cl 4-C₄H₉-t 224-226 89 i-C₃H₇ H H 3-Cl 4-CF(CF₃)₂ 198-200 90 i-C₃H₇ H H 3-Cl 4-CF₂CF₂CF₃ 203-204 91 i-C₃H₇ H H 3-Cl 4-(CF₂)₃CF₃ 176-178 92 i-C₃H₇ H H 3-Cl 4-OCHF₂ 205-207 93 i-C₃H₇ H H 3-Cl 4-OCF₂CHFOC₃F₇-n 169-171 94 i-C₃H₇ H H 3-Cl 4-SCH₃ 231-232 95 i-C₃H₇ H H 6-Cl 4-SCH₃ 193-195 96 i-C₃H₇ H H 3-Cl 4-SOCH₃ 178-182 97 i-C₃H₇ H H 3-Cl 4-SO₂CH₃ 208-210 98 i-C₃H₇ H H 3-Cl 4-SCHF₂ 220-222 99 i-C₃H₇ H H 3-Cl 3-SCF₃ 189-191 100 i-C₃H₇ H H 3-Cl 3-SOCF₃ 183-187 101 i-C₃H₇ H H 3-Cl 4-SCH₂CF₃ 191-193 102 i-C₃H₇ H H 3-Cl 4-SCF₂CHF₂ 198-200 103 i-C₃H₇ H H 3-Cl 4-SCF₂CBrF₂ 201-203 104 i-C₃H₇ H H 3-Cl 4-SCF(CF₃)₂ 221-223 105 i-C₃H₇ H H 3-Cl 4-S(CF₂)₃CF₃ 199-200 106 i-C₃H₇ H H 3-Cl 4-SOCF(CF₃)₂ 204-206 107 i-C₃H₇ H H 3-Cl 4-SO₂CH₂CF₃ 202-204 108 i-C₃H₇ H H 3-Cl 4-SO₂CF₂CHF₂ 227-230 109 i-C₃H₇ H H 3-Cl 4-COCH₃ 217-219 110 i-C₃H₇ H H 3-Cl 4-Ph 215-217 111 i-C₃H₇ H H 3-Cl 2,3-Cl₂ 168-169 112 i-C₃H₇ H H 3-Cl 2,4-Cl₂ 190-192 113 i-C₃H₇ H H 3-Cl 2,4-F₂ 188-190 114 i-C₃H₇ H H 3-Cl 2-Cl-4-F 172-173 115 i-C₃H₇ H H 3-Cl 2-F-4-Cl 181-182 116 i-C₃H₇ H H 3-Cl 2,3,4-F₃ 174-176 117 i-C₃H₇ H H 3-Cl 2,3-(CH₃)₂ 187-189 118 i-C₃H₇ H H 3-Cl 2-CH₃-3-Cl 200-202 119 i-C₃H₇ H H 3-Cl 2-CH₃-4-Cl 213-215 120 i-C₃H₇ H H 3-Cl 2-CH₃-5-Cl 183-185 121 i-C₃H₇ H H 3-Cl 2-CH₃-4-Br 210-212 122 i-C₃H₇ H H 3-Cl 2-CH₃-4-I 206-208 123 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCH₃ 191-192 124 i-C₃H₇ H H 3-Cl 2,3-(CH₃)₂-4-OCH₃ 208-210 125 i-C₃H₇ H H 3-Cl 2-Cl-4-CF₃ 156-157 126 i-C₃H₇ H H 3-Cl 2-Cl-4-CF(CF₃)₂ 204-206 127 i-C₃H₇ H H 3-Cl 2-CH₃-4-CF₃ 219-220 128 i-C₃H₇ H H 3-Cl 2-CH₃-4-CF₂CF₃ 199-200 129 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₂CCl₃ 169-171 130 i-C₃H₇ H H 3-Cl 2-CH₃-4-CF₂CF₂CF₃ 214-215 131 i-C₃H₇ H H 3-Cl 2-CH₃-4-CF(CF₃)₂ 220-222 132 i-C₃H₇ H H 3-Cl 2-CH₃-4-(CF₂)₃CF₃ 188-189 133 i-C₃H₇ H H 3-Cl 2-CH₃-4-(CF₂)₅CF₃ 161-163 134 i-C₃H₇ H H 3-Cl 3-Cl-4-OCHF₂ 197-199 135 i-C₃H₇ H H 3-Cl 2-Cl-4-OCF₃ 158-159 136 i-C₃H₇ H H 3-Cl 2-Br-4-OCF₃ 169-170 137 i-C₃H₇ H H 3-Cl 3-F-4-OCHF₂ 211-212 138 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCHF₂ 193-195 139 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₃ 199-201 140 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCBrF₂ 181-182 141 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₂CHF₂ 202-204 142 i-C₃H₇ H H 3-Cl 2-CH₃-3-OCF₂CHClF 169-171 143 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₂CHClF 194-196 144 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₂CBrF₂ 193-194 145 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₂CCl₂F 202-203 146 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₂CHFCF₃ 186-187 147 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCH₂CF₂CHF₂ 207-208 148 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₂CBrFCF₃ 205-206 149 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₂CHFOCF₃ 179-181 150 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCHF₂-5-Cl 191-192 151 i-C₃H₇ H H 3-Cl 3,5-Cl₂-4-OCHF₂ 205-207 152 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₂CHF₂-5-Cl 211-212 153 i-C₃H₇ H H 3-Cl 2-CH₃-4-SC₃H₇-i 189-191 154 i-C₃H₇ H H 3-Cl 2-CH₃-4-SCHF₂ 189-191 155 i-C₃H₇ H H 3-Cl 2-CH₃-4-SOCHF₂ 173-176 156 i-C₃H₇ H H 3-Cl 2-CH₃-4-SO₂CHF₂ 168-170 157 i-C₃H₇ H H 3-Cl 2-CH₃-4-(F₅—PhO) 224-226 158 i-C₃H₇ H H 3-Cl 2-CH₃-4-(5-CF₃-2-Pyi-O) 189-191 159 i-C₃H₇ H H 3-Cl 2-CH₃-4-(3-Cl- 204-205 5-CF₃-2-Pyi-O) 160 i-C₃H₇ H H 3-Cl 4-(3-Cl-5-CF₃-2-Pyi-S) 213-215 161 i-C₃H₇ H H 3-Cl 2-CH₃-4-P═O(OC₂H₅)₂ 71-73 162 i-C₃H₇ H H 3-Cl 2-CH₃-4-OP═S(OCH₃)₂ 168-170 163 i-C₃H₇ H H 3-Cl 2-CF₃-4-OCHF₂ 194-196 164 i-C₃H₇ H H 3-Cl 3-CF₃-4-OCHF₂ 208-209 165 i-C₃H₇ H H 3-Cl 3-N═C(CF₃)—O-4 248-250 166 i-C₃H₇ H H 3-Cl 3-N═C(CF₃)—NH-4 194-196 167 i-C₃H₇ H H 3-Cl 3-N═C(CF₃)—N(CH₃)-4 225-227 168 i-C₃H₇ H H 4-Cl H 190-192 169 i-C₃H₇ H H 4-Cl 4-F 213-215 170 i-C₃H₇ H H 4-Cl 2-CH₃ 208-210 171 i-C₃H₇ H H 4-Cl 3-CF₃ 196-198 172 i-C₃H₇ H H 4-Cl 4-OCF₃ 192-194 173 i-C₃H₇ H H 4-Cl 2,4-Cl₂ 174-176 174 i-C₃H₇ H H 4-Cl 3,4-F₂ 231-233 175 i-C₃H₇ H H 4-Cl 2,3-Cl₂ 186-188 176 i-C₃H₇ H H 4-Cl 2-CH₃-3-Cl 203-205 177 i-C₃H₇ H H 4-Cl 2-CH₃-4-Cl 206-208 178 i-C₃H₇ H H 4-Cl 2-CH₃-5-Cl 207-208 179 i-C₃H₇ H H 4-Cl 2-CH₃-5-F 229-231 180 i-C₃H₇ H H 4-Cl 2-CH₃-4-OCHF₂ 223-224 181 i-C₃H₇ H H 5-Cl H 186-188 182 i-C₃H₇ H H 5-Cl 4-F 209-211 183 i-C₃H₇ H H 5-Cl 2-CH₃ 187-189 184 i-C₃H₇ H H 5-Cl 3-CF₃ 198-200 185 i-C₃H₇ H H 5-Cl 4-OCF₃ 180-182 186 i-C₃H₇ H H 5-Cl 2,3-Cl₂ 167-169 187 i-C₃H₇ H H 5-Cl 2,4-Cl₂ 165-167 188 i-C₃H₇ H H 5-Cl 3,4-F₂ 207-209 189 i-C₃H₇ H H 5-Cl 2-CH₃-3-Cl 204-206 190 i-C₃H₇ H H 5-Cl 2-CH₃-4-Cl 202-204 191 i-C₃H₇ H H 5-Cl 2-CH₃-5-Cl 209-210 192 i-C₃H₇ H H 5-Cl 2-CH₃-5-F 192-194 193 i-C₃H₇ H H 5-Cl 2-CH₃-4-OCHF₂ 188-189 194 i-C₃H₇ H H 5-Cl 2,3,4-F₃ 224-226 195 i-C₃H₇ H H 6-Cl 4-C₄H₉-n 194-196 196 i-C₃H₇ H H 6-Cl 4-C₄H₉-t 235-237 197 i-C₃H₇ H H 6-Cl 4-CF₂CF₂CF₃ 216-217 198 i-C₃H₇ H H 6-Cl 4-CF(CF₃)₂ 209-211 199 i-C₃H₇ H H 6-Cl 4-(CF₂)₃CF₃ 196-198 200 i-C₃H₇ H H 6-Cl 4-OCHF₂ 223-225 201 i-C₃H₇ H H 6-Cl 4-OCF₂CHFOC₃F₇-n 205-207 202 i-C₃H₇ H H 6-Cl 4-SCH₂CF₃ 189-190 203 i-C₃H₇ H H 6-Cl 4-SCF₂CHF₂ 211-213 204 i-C₃H₇ H H 6-Cl 4-SCF(CF₃)₂ 250-252 205 i-C₃H₇ H H 6-Cl 4-S(CF₂)₃CF₃ 210-212 206 i-C₃H₇ H H 6-Cl 3-SOCF₃ 212-215 207 i-C₃H₇ H H 6-Cl 4-COCH₃ 230-232 208 i-C₃H₇ H H 6-Cl 2,3-Cl₂ 179-180 209 i-C₃H₇ H H 6-Cl 2,4-Cl₂ 199-200 210 i-C₃H₇ H H 6-Cl 2,4-F₂ 196-198 211 i-C₃H₇ H H 6-Cl 2-Cl-4-F 196-197 212 i-C₃H₇ H H 6-Cl 2-F-4-Cl 184-186 213 i-C₃H₇ H H 6-Cl 2,3-(CH₃)₂ 214-216 214 i-C₃H₇ H H 6-Cl 2-CH₃-4-Cl 233-235 215 i-C₃H₇ H H 6-Cl 2-CH₃-5-Cl 204-206 216 i-C₃H₇ H H 6-Cl 2-CH₃-4-Br 242-244 217 i-C₃H₇ H H 6-Cl 2-CH₃-4-I 236-238 218 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCH₃ 195-197 219 i-C₃H₇ H H 6-Cl 2,3-(CH₃)₂-4-OCH₃ 242-244 220 i-C₃H₇ H H 6-Cl 2-Cl-4-CF₃ 171-172 221 i-C₃H₇ H H 6-Cl 2-CH₃-4-CF₃ 234-236 222 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCF₂CCl₃ 169-171 223 i-C₃H₇ H H 6-Cl 2-CH₃-4-CF₂CF₃ 215-217 224 i-C₃H₇ H H 6-Cl 2-CH₃-4-CF(CF₃)₂ 238-240 225 i-C₃H₇ H H 6-Cl 2-CH₃-4-(CF₂)₃CF₃ 177-178 226 i-C₃H₇ H H 6-Cl 2-CH₃-4-(CF₂)₅CF₃ 167-169 227 i-C₃H₇ H H 6-Cl 3,5-Cl₂-4-OCHF₂ 196-198 228 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCF₂CCl₂F 218-220 229 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCF₂CBrF₂ 214-215 230 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCH₂CF₂CHF₂ 212-213 231 i-C₃H₇ H H 6-Cl 2-Cl-4-CF(CF₂)₂ 212-214 232 i-C₃H₇ H H 6-Cl 3-Cl-4-OCHF₂ 204-206 233 i-C₃H₇ H H 6-Cl 3-F-4-OCHF₂ 225-227 234 i-C₃H₇ H H 6-Cl 2-Cl-4-OCF₃ 161-162 235 i-C₃H₇ H H 6-Cl 2-Br-4-OCF₃ 188-189 236 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCHF₂ 213-215 237 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCF₃ 212-214 238 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCBrF₂ 195-196 239 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCF₂CHF₂ 199-201 240 i-C₃H₇ H H 6-Cl 2-CH₃-3-OCF₂CHClF 195-197 241 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCF₂CHClF 204-213 242 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCF₂CHFCF₃ 199-200 243 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCF₂CBrFCF₃ 226-227 244 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCF₂CHFOCF₃ 210-212 245 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCHF₂-5-Cl 234-235 246 i-C₃H₇ H H 6-Cl 2-CH₃-4-OCF₂CHF₂-5-Cl 230-232 247 i-C₃H₇ H H 6-Cl 2-CH₃-4-SCHF₂ 199-201 248 i-C₃H₇ H H 6-Cl 2-CH₃-4-(F₅—PhO) 243-245 249 i-C₃H₇ H H 6-Cl 2-CH₃-4-(5-CF₃-2-Pyi-O) 116-120 250 i-C₃H₇ H H 6-Cl 2-CH₃-4-(3-Cl- 219-221 5-CF₃-2-Pyi-O) 251 i-C₃H₇ H H 6-Cl 2-CH₃-4-P═O(OC₂H₅)₂ 146-147 252 i-C₃H₇ H H 6-Cl 2-CH₃-4-OP═S(OCH₃)₂ 183-185 253 i-C₃H₇ H H 6-Cl 2-CF₃-4-OCHF₂ 234-236 254 i-C₃H₇ H H 6-Cl 3-CF₃-4-OCHF₂ 204-205 255 i-C₃H₇ H H 6-Cl 3-N═C(CF₃)—O-4 270-272 256 i-C₃H₇ H H 6-Cl 3-N═C(CF₃)—NH-4 213-215 257 i-C₃H₇ H H 6-Cl 3-N═C(CF₃)—N(CH₃)-4 239-241 258 i-C₃H₇ H H 3,6-Cl₂ 2-CH₃-4-OCHF₂ 221-222 259 i-C₃H₇ H H 3,6-Cl₂ 2-CH₃-4-Cl 234-235 260 i-C₃H₇ H H 3,4,5,6-Cl₄ 2-CH₃-4-Cl 265-266 261 i-C₃H₇ H H 3-Br 4-CF₃ 221-223 262 i-C₃H₇ H H 3-Br 4-OCF₃ 208-210 263 i-C₃H₇ H H 3-Br 2,3-(CH₃)₂ 248-250 264 i-C₃H₇ H H 3-Br 2,4-(CH₃)₂ 223-224 265 i-C₃H₇ H H 3-Br 2,4,6-(CH₃)₃ 254-255 266 i-C₃H₇ H H 3-Br 2-CH₃-3-Cl 215-217 267 i-C₃H₇ H H 3-Br 2-CH₃-4-Cl 176-178 268 i-C₃H₇ H H 3-Br 2-CH₃-5-Cl 196-198 269 i-C₃H₇ H H 3-Br 2,3-(CH₃)₂-4-Cl 222-224 270 i-C₃H₇ H H 3-Br 2,4-(CH₃)₂-3-Cl 236-238 271 i-C₃H₇ H H 3-Br 2-C₂H₅-4-Cl 205-207 272 i-C₃H₇ H H 3-Br 2-CH₃-4-Br 220-222 273 i-C₃H₇ H H 3-Br 2,3-(CH₃)₂-4-Br 200-202 274 i-C₃H₇ H H 3-Br 2-CH₃-4-I 203-205 275 i-C₃H₇ H H 3-Br 2-CH₃-4-F 223-224 276 i-C₃H₇ H H 3-Br 2-Cl-4-CF₃ 156-157 277 i-C₃H₇ H H 3-Br 2-CH₃-4-CF₃ 227-228 278 i-C₃H₇ H H 3-Br 2-CH₃-4-CF₂CF₃ 201-202 279 i-C₃H₇ H H 3-Br 2-CH₃-4-CF₂CF₂CF₃ 199-200 280 i-C₃H₇ H H 3-Br 2-CH₃-4-CF(CF₃)₂ 222-224 281 i-C₃H₇ H H 3-Br 2-CH₃-4-(CF₂)₃CF₃ 190-191 282 i-C₃H₇ H H 3-Br 2-CH₃-4-OCH₃ 199-200 283 i-C₃H₇ H H 3-Br 2-CH₃-4-OCH₂CF₂CHF₂ 206-207 284 i-C₃H₇ H H 3-Br 2,4-(CH₃)₂-3-OCHF₂ 187-189 285 i-C₃H₇ H H 3-Br 2,3-(CH₃)₂-4-OCH₃ 206-208 286 i-C₃H₇ H H 3-Br 2-Cl-4-OCF₃ 165-167 287 i-C₃H₇ H H 3-Br 2-Br-4-OCF₃ 179-180 288 i-C₃H₇ H H 3-Br 2-CH₃-4-OCHF₂ 205-207 289 i-C₃H₇ H H 3-Br 2-CH₃-4-OCF₃ 211-213 290 i-C₃H₇ H H 3-Br 2-CH₃-4-OCBrF₂ 178-180 291 i-C₃H₇ H H 3-Br 2-CH₃-4-OCF₂CHFCF₃ 196-197 292 i-C₃H₇ H H 3-Br 2-CH₃-4-OCF₂CHClF 194-195 293 i-C₃H₇ H H 3-Br 2-CH₃-4-OCF₂CHF₂ 205-207 294 i-C₃H₇ H H 3-Br 2-CH₃-3-Cl-4-OCHF₂ 229-230 295 i-C₃H₇ H H 3-Br 2,3-(CH₃)₂-4-OCHF₂ 219-220 296 i-C₃H₇ H H 3-Br 2-CH₃-4-SCH₃ 215-217 297 i-C₃H₇ H H 3-Br 2-CH₃-4-(3-CF₃—PhO) 156-158 298 i-C₃H₇ H H 3-Br 2-CH₃-4-(3-Cl- 206-208 5-CF₃-2-Pyi-O) 299 i-C₃H₇ H H 3-Br 2-CH₃-4-(5-CF₃- 182-184 2-Pyi-O) 300 i-C₃H₇ H H 3-Br -3-OCH₂O-4- 195-198 301 i-C₃H₇ H H 6-Br 4-CF₃ 190-192 302 i-C₃H₇ H H 6-Br 4-OCF₃ 210-212 303 i-C₃H₇ H H 6-Br 2,3-(CH₃)₂ 250-252 304 i-C₃H₇ H H 6-Br 2,4,6-(CH₃)₃ 272-274 305 i-C₃H₇ H H 6-Br 2-CH₃-3-Cl 214-216 306 i-C₃H₇ H H 6-Br 2-CH₃-4-Cl 198-200 307 i-C₃H₇ H H 6-Br 2-CH₃-5-Cl 194-196 308 i-C₃H₇ H H 6-Br 2,3-(CH₃)₂-4-Cl 227-229 309 i-C₃H₇ H H 6-Br 2,4-(CH₃)₂-3-Cl 249-251 310 i-C₃H₇ H H 6-Br 2-C₂H₅-4-Cl 243-245 311 i-C₃H₇ H H 6-Br 2-CH₃-4-Br 227-228 312 i-C₃H₇ H H 6-Br 2,3-(CH₃)₂-4-Br 209-211 313 i-C₃H₇ H H 6-Br 2-CH₃-4-I 227-229 314 i-C₃H₇ H H 6-Br 2-CH₃-4-F 231-232 315 i-C₃H₇ H H 6-Br 2-Cl-4-CF₃ 169-170 316 i-C₃H₇ H H 6-Br 2-CH₃-4-CF₃ 232-234 317 i-C₃H₇ H H 6-Br 2-CH₃-4-CF(CF₃)₂ 236-238 318 i-C₃H₇ H H 6-Br 2-CH₃-4-(CF₂)₃CF₃ 208-210 319 i-C₃H₇ H H 6-Br 2-CH₃-4-OCH₂CF₂CHF₂ 209-211 320 i-C₃H₇ H H 6-Br 2,4-(CH₃)₂-3-OCHF₂ 247-249 321 i-C₃H₇ H H 6-Br 2,3-(CH₃)₂-4-OCH₃ 250-252 322 i-C₃H₇ H H 6-Br 2-CH₃-4-OCH₃ 220-222 323 i-C₃H₇ H H 6-Br 2-Cl-4-OCF₃ 182-183 324 i-C₃H₇ H H 6-Br 2-Br-4-OCF₃ 195-196 325 i-C₃H₇ H H 6-Br 2-CH₃-4-OCHF₂ 225-226 326 i-C₃H₇ H H 6-Br 2-CH₃-4-OCF₃ 223-225 327 i-C₃H₇ H H 6-Br 2-CH₃-4-OCBrF₂ 194-196 328 i-C₃H₇ H H 6-Br 2-CH₃-4-OCF₂CHFCF₃ 212-213 329 i-C₃H₇ H H 6-Br 2-CH₃-4-OCF₂CHClF 211-213 330 i-C₃H₇ H H 6-Br 2-CH₃-4-OCF₂CHF₂ 214-215 331 i-C₃H₇ H H 6-Br 2,3-(CH₃)₂-4-OCHF₂ 228-229 332 i-C₃H₇ H H 6-Br 2-CH₃-3-Cl-4-OCHF₂ 224-225 333 i-C₃H₇ H H 6-Br 2-CH₃-4-SCH₃ 215-217 334 i-C₃H₇ H H 6-Br 2-CH₃-4-(3-CF₃—PhO) 194-195 335 i-C₃H₇ H H 6-Br 2-CH₃-4-(5-CF₃- 201-203 -2-Pyi-O) 336 i-C₃H₇ H H 6-Br 2-CH₃-4-(3-Cl-5- 234-236 CF₃-2-Pyi-O) 337 i-C₃H₇ H H 6-Br -3-OCH₂O-4- 205-207 338 i-C₃H₇ H H 3,4-Br₂ 2-CH₃-4-OCHF₂ 196-197 339 i-C₃H₇ H H 3,4-Br₂ 2-CH₃-4-Cl 199-201 340 i-C₃H₇ H H 3,6-Br 2-CH₃-4-OCHF₂ 233-234 341 i-C₃H₇ H H 3,6-Br₂ 2-CH₃-4-Cl 245-247 342 i-C₃H₇ H H 5,6-Br₂ 2-CH₃-4-OCHF₂ 208-210 343 i-C₃H₇ H H 5,6-Br₂ 2-CH₃-4-Cl 259-261 344 i-C₃H₇ H H 3,4,5,6-Br₄ 2-CH₃-4-Cl 270-272 345 i-C₃H₇ H H 3-I 4-Cl 230-232 346 i-C₃H₇ H H 3-I 4-Br 251-253 347 i-C₃H₇ H H 3-I 4-I 231-233 348 i-C₃H₇ H H 3-I 3-CF₃ 194-197 349 i-C₃H₇ H H 3-I 4-CF₃ 223-224 350 i-C₃H₇ H H 3-I 4-CF₂CF₂CF₃ 217-219 351 i-C₃H₇ H H 3-I 4-CF(CF₃)₂ 209-211 352 i-C₃H₇ H H 3-I 4-OCF₃ 222-223 353 i-C₃H₇ H H 3-I 4-OCF₂CHFOCF₃ 192-194 354 i-C₃H₇ H H 3-I 4-SCHF₂ 204-206 355 i-C₃H₇ H H 3-I 4-SCH₂CF₃ 195-197 356 i-C₃H₇ H H 3-I 4-SCF₂CHF₂ 196-198 357 i-C₃H₇ H H 3-I 4-SCF₂CBrF₂ 203-205 358 i-C₃H₇ H H 3-I 4-SCF(CF₃)₂ 170-172 359 i-C₃H₇ H H 3-I 4-S(CF₂)₃CF₃ 185-187 360 i-C₃H₇ H H 3-I 3,4-F₂ 227-229 361 i-C₃H₇ H H 3-I 2-CH₃-3-Cl 222-224 362 i-C₃H₇ H H 3-I 2-CH₃-4-Cl 215-217 363 i-C₃H₇ H H 3-I 2-CH₃-5-Cl 210-212 364 i-C₃H₇ H H 3-I 2,4-(CH₃)₂-3-Cl 226-228 365 i-C₃H₇ H H 3-I 2,3-(CH₃)₂-4-Cl 235-237 366 i-C₃H₇ H H 3-I 2-CH₃-4-Br 227-229 367 i-C₃H₇ H H 3-I 2-CH₃-4-I 201-203 368 i-C₃H₇ H H 3-I 2-CH₃-4-F 227-228 369 i-C₃H₇ H H 3-I 2-Cl-4-CF₃ 170-171 370 i-C₃H₇ H H 3-I 2-CH₃-3-CF₃ 179-181 371 i-C₃H₇ H H 3-I 2-CH₃-4-CF₃ 202-203 372 i-C₃H₇ H H 3-I 2-CH₃-4-CF₂CF₃ 195-196 373 i-C₃H₇ H H 3-I 2-CH₃-4-CF₂CF₂CF₃ 193-195 374 i-C₃H₇ H H 3-I 2-CH₃-4-CF(CF₃)₂ 211-213 375 i-C₃H₇ H H 3-I 2-CH₃-4-(CF₂)₃CF₃ 203-204 376 i-C₃H₇ H H 3-I 2-CH₃-4-OCH₃ 204-206 377 i-C₃H₇ H H 3-I 2-CH₃-4-O—C₃H₇-i 209-211 378 i-C₃H₇ H H 3-I 2,3-(CH₃)₂-4-OCH₃ 220-222 379 i-C₃H₇ H H 3-I 2-CH₃-4-OCH₂CF₃ 223-224 380 i-C₃H₇ H H 3-I 2-CH₃-4-OCF₂CBrF₂ 228-230 381 i-C₃H₇ H H 3-I 2-CH₃-4-OCF₂CCl₂F 230-231 382 i-C₃H₇ H H 3-I 3-F-4-OCHF₂ 208-210 383 i-C₃H₇ H H 3-I 3,5-Cl₂-4-OCHF₂ 234-236 384 i-C₃H₇ H H 3-I 3-OCH₃-4-OCHF₂ 196-198 385 i-C₃H₇ H H 3-I 3,4-(OCHF₂)₂ 171-172 386 i-C₃H₇ H H 3-I 2-CH₃-4-OCF₃ 214-216 387 i-C₃H₇ H H 3-I 2-CH₃-4-OCHF₂ 207-209 388 i-C₃H₇ H H 3-I 2-CH₃-4-OCH₂CF₂CHF₂ 229-231 389 i-C₃H₇ H H 3-I 2-CH₃-4-OCBrF₂ 181-182 390 i-C₃H₇ H H 3-I 2-CH₃-4-OCF₂CHF₂ 197-199 391 i-C₃H₇ H H 3-I 2-CH₃-4-OCF₂CHF₂-5-Cl 198-200 392 i-C₃H₇ H H 3-I 2-CH₃-4-OCF₂CHClF 200-201 393 i-C₃H₇ H H 3-I 2-CH₃-4-OCF₂CHFCF₃ 213-214 394 i-C₃H₇ H H 3-I 2-CH₃-4-OCF₂CBrFCF₃ 233-234 395 i-C₃H₇ H H 3-I 2-CH₃-4-OCF₂CHFOCF₃ 213-215 396 i-C₃H₇ H H 3-I 2-CH₃-4-OCHF₂-5-Cl 230-232 397 i-C₃H₇ H H 3-I 2-CH₃-4-(F₅—PhO) 245-247 398 i-C₃H₇ H H 3-I 2-CH₃-4-(3-CF₃—PhO) 168-170 399 i-C₃H₇ H H 3-I 2-CH₃-4-(5-CF₃-2- 186-188 Pyi-O) 400 i-C₃H₇ H H 3-I 2-CH₃-4-(3-Cl-5-CF₃- 212-214 2-Pyi-O) 401 i-C₃H₇ H H 3-I 2-CH₃-4-SO₂CH₃ 172-175 402 i-C₃H₇ H H 3-I 2-CH₃-4-SC₃H₇-i 190-192 403 i-C₃H₇ H H 3-I 2-CH₃-4-SCF₂CF₂CF₃ 227-228 404 i-C₃H₇ H H 3-I 2-CH₃-4-(4-Cl—PhS) 191-192 405 i-C₃H₇ H H 3-I 4-(3-Cl-5-CF₃-2-Pyi-S) 198-200 406 i-C₃H₇ H H 3-I 2-Br-4-OCF₃ 196-198 407 i-C₃H₇ H H 3-I 2-Cl-4-CF₂CF₂CF₃ 162-164 408 i-C₃H₇ H H 3-I 2-Cl-4-OCF₃ 173-175 409 i-C₃H₇ H H 3-I 2-CF₃-4-OCHF₂ 219-220 410 i-C₃H₇ H H 3-I 3-CF₃-4-OCHF₂ 128-130 411 i-C₃H₇ H H 6-I 4-Cl 251-253 412 i-C₃H₇ H H 6-I 4-Br 270-272 413 i-C₃H₇ H H 6-I 4-I 242-244 414 i-C₃H₇ H H 6-I 3-CF₃ 210-212 415 i-C₃H₇ H H 6-I 4-CF₃ 201-202 416 i-C₃H₇ H H 6-I 4-CF(CF₃)₂ 238-240 417 i-C₃H₇ H H 6-I 4-CF₂CF₂CF₃ 238-240 418 i-C₃H₇ H H 6-I 4-OCF₃ 193-194 419 i-C₃H₇ H H 6-I 4-OCF₂CHFOC₃F₇-n 213-214 420 i-C₃H₇ H H 6-I 4-SCH₂CF₃ 217-219 421 i-C₃H₇ H H 6-I 4-SCHF₂ 224-226 422 i-C₃H₇ H H 6-I 4-SCF₂CHF₂ 213-215 423 i-C₃H₇ H H 6-I 4-SCF₂CBrF₂ 220-222 424 i-C₃H₇ H H 6-I 4-SCF₂CF₂CF₃ 196-197 425 i-C₃H₇ H H 6-I 4-SCF(CF₃)₂ 216-218 426 i-C₃H₇ H H 6-I 4-S(CF₂)₃CF₃ 201-203 427 i-C₃H₇ H H 6-I 2-CH₃-3-Cl 252-254 428 i-C₃H₇ H H 6-I 2-CH₃-4-Cl 244-246 429 i-C₃H₇ H H 6-I 2,4-(CH₃)₂-3-Cl 260-262 430 i-C₃H₇ H H 6-I 2-CH₃-4-Br 241-243 431 i-C₃H₇ H H 6-I 2-CH₃-4-I 213-215 432 i-C₃H₇ H H 6-I 2-CH₃-4-F 251-252 433 i-C₃H₇ H H 6-I 2-Cl-4-CF₃ 195-196 434 i-C₃H₇ H H 6-I 2,3-(CH₃)₂-4-Cl 253-255 435 i-C₃H₇ H H 6-I 2-CH₃-3-CF₃ 245-251 436 i-C₃H₇ H H 6-I 2-CH₃-4-CF₃ 220-221 437 i-C₃H₇ H H 6-I 2-CH₃-4-CF₂CF₃ 203-205 438 i-C₃H₇ H H 6-I 2-CH₃-4-CF₂CF₂CF₃ 154-156 439 i-C₃H₇ H H 6-I 2-CH₃-4-CF(CF₃)₂ 237-239 440 i-C₃H₇ H H 6-I 2-CH₃-4-(CF₂)₃CF₃ 168-170 441 i-C₃H₇ H H 6-I 2-CH₃-4-OCH₃ 215-217 442 i-C₃H₇ H H 6-I 2-CH₃-4-O—C₃H₇-i 212-214 443 i-C₃H₇ H H 6-I 2-CH₃-4-OCH₂CF₃ 233-234 444 i-C₃H₇ H H 6-I 2-CH₃-4-OCF₂CBrF₂ 242-244 445 i-C₃H₇ H H 6-I 2-CH₃-4-OCF₂CCl₂F 251-253 446 i-C₃H₇ H H 6-I 2-CH₃-4-OCF₂CBrFCF₃ 251-253 447 i-C₃H₇ H H 6-I 2-CH₃-4-OCH₂CF₂CHF₂ 235-237 448 i-C₃H₇ H H 6-I 3-F-4-OCHF₂ 214-216 449 i-C₃H₇ H H 6-I 3,5-Cl₂-4-OCHF₂ 211-213 450 i-C₃H₇ H H 6-I 3-OCH₃-4-OCHF₂ 215-217 451 i-C₃H₇ H H 6-I 2,3-(CH₃)₂-4-OCH₃ 253-254 452 i-C₃H₇ H H 6-I 2-CH₃-4-OCBrF₂ 192-194 453 i-C₃H₇ H H 6-I 2-CH₃-4-OCF₂CHF₂ 216-218 454 i-C₃H₇ H H 6-I 2-CH₃-4-OCF₂CHF₂-5-Cl 230-232 455 i-C₃H₇ H H 6-1 2-CH₃-4-OCF₂CHClF 205-207 456 i-C₃H₇ H H 6-I 2-CH₃-4-OCF₂CHFCF₃ 222-223 457 i-C₃H₇ H H 6-I 2-CH₃-4-OCF₂CHFOCF₃ 258-260 458 i-C₃H₇ H H 6-I 2-CH₃-4-(3-CF₃—PhO) 198-199 459 i-C₃H₇ H H 6-I 2-CH₃-4-(F₅—PhO) 262-264 460 i-C₃H₇ H H 6-I 2-CH₃-4-(5-CF₃-2-Pyi-O) 245-246 461 i-C₃H₇ H H 6-I 2-CH₃-4-(3-Cl- 231-232 5-CF₃-2-Pyi-O) 462 i-C₃H₇ H H 6-I 2-CH₃-4-SC₃H₇-i 197-199 463 i-C₃H₇ H H 6-I 2-CH₃-4-(4-Cl—PhS) 211-213 464 i-C₃H₇ H H 6-I 2-CH₃-4-OCF₃ 230-232 465 i-C₃H₇ H H 6-I 2-CF₃-4-OCHF₂ 238-239 466 i-C₃H₇ H H 6-I 2-Br-4-OCF₃ 215-217 467 i-C₃H₇ H H 6-I 2-Cl-4-OCF₃ 186-188 468 i-C₃H₇ H H 6-I 2-Cl-4-CF₂CF₂CF₃ 199-200 469 i-C₃H₇ H H 6-I 2-CH₃-4-OCHF₂ 226-228 470 i-C₃H₇ H H 6-I 2-CH₃-4-OCHF₂-5-Cl 239-240 471 i-C₃H₇ H H 6-I 3-CF₃-4-OCHF₂ 238-239 472 i-C₃H₇ H H 3-F 4-(CF₂)₃CF₃ 187-188 473 i-C₃H₇ H H 3-F 4-CF₂CF₂CF₃ 182-183 474 i-C₃H₇ H H 3-F 4-CF(CF₃)₂ 206-208 475 i-C₃H₇ H H 3-F 4-OCF₃ 197-199 476 i-C₃H₇ H H 3-F 4-OCF₂CHFOC₃F₇-n 142-144 477 i-C₃H₇ H H 3-F 4-SCHF₂ 190-192 478 i-C₃H₇ H H 3-F 4-SCH₂CF₃ 157-158 479 i-C₃H₇ H H 3-F 4-SCF₂CHF₂ 177-178 480 i-C₃H₇ H H 3-F 4-SCF₂CBrF₂ 197-199 481 i-C₃H₇ H H 3-F 4-SCF(CF₃)₂ 206-208 482 i-C₃H₇ H H 3-F 4-S(CF₂)₃CF₃ 173-174 483 i-C₃H₇ H H 3-F 4-SOCH₂CF₃ 115-119 484 i-C₃H₇ H H 3-F 4-SOCF₂CBrF₂ 181-182 485 i-C₃H₇ H H 3-F 4-SOCF(CF₃)₂ 195-197 486 i-C₃H₇ H H 3-F 4-SO(CF₂)₃CF₃ 175-176 487 i-C₃H₇ H H 3-F 4-SO₂CH₂CF₃ 199-202 488 i-C₃H₇ H H 3-F 2,3-Cl₂ 175-177 489 i-C₃H₇ H H 3-F 2-CH₃-3-Cl 193-194 490 i-C₃H₇ H H 3-F 2-CH₃-4-Cl 192-194 491 i-C₃H₇ H H 3-F 2-CH₃-5-Cl 191-193 492 i-C₃H₇ H H 3-F 2-CH₃-4-I 192-194 493 i-C₃H₇ H H 3-F 2-CH₃-5-F 175-177 494 i-C₃H₇ H H 3-F 2-CH₃-3-F 187-189 495 i-C₃H₇ H H 3-F 2-CH₃-4-CF₂CF₃ 213-214 496 i-C₃H₇ H H 3-F 2-CH₃-4-CF₂CF₂CF₃ 191-192 497 i-C₃H₇ H H 3-F 2-CH₃-4-CF(CF₃)₂ 241-243 498 i-C₃H₇ H H 3-F 2-CH₃-4-(CF₂)₃CF₃ 138-139 499 i-C₃H₇ H H 3-F 2-CH₃-3-OCHF₂ 172-174 500 i-C₃H₇ H H 3-F 2-CH₃-4-OCHF₂ 160-162 501 i-C₃H₇ H H 3-F 2-CH₃-4-OCF₂CCl₃ 162-163 502 i-C₃H₇ H H 3-F 2-CH₃-4-OCF₂CCl₂F 207-208 503 i-C₃H₇ H H 3-F 2-CH₃-4-OCF₂CBrF₂ 196-197 504 i-C₃H₇ H H 3-F 2-Cl-4-CF₃ 169-170 505 i-C₃H₇ H H 3-F 2-Cl-4-CF₂CF₂CF₃ 169-170 506 i-C₃H₇ H H 3-F 3,5-Cl₂-4-OCHF₂ 201-202 507 i-C₃H₇ H H 3-F 2-Cl-4-CF(CF₃)₂ 223-225 508 i-C₃H₇ H H 3-F 2-Cl-4-OCF₃ 169-170 509 i-C₃H₇ H H 3-F 2-Br-4-OCF₃ 164-165 510 i-C₃H₇ H H 3-F 2-CH₃-4-OCF₃ 183-184 511 i-C₃H₇ H H 3-F 2-CH₃-4-OCBrF₂ 177-178 512 i-C₃H₇ H H 3-F 2-CH₃-4-OCF₂CHF₂ 172-173 513 i-C₃H₇ H H 3-F 2-CH₃-4-OCF₂CHClF 168-169 514 i-C₃H₇ H H 3-F 2-CH₃-4-OCF₂CHFCF₃ 160-162 515 i-C₃H₇ H H 3-F 2-CH₃-4-OCF₂CHFOCF₃ 148-150 516 i-C₃H₇ H H 3-F 2-CH₃-4-OCF₂CBrFCF₃ 148-150 517 i-C₃H₇ H H 3-F 2-CH₃-4-OCHF₂-5-Cl 187-188 518 i-C₃H₇ H H 3-F 2-CH₃-4-SC₃H₇-i 165-167 519 i-C₃H₇ H H 3-F 2-CH₃-4-(3-CF₃—PhO) 135-136 520 i-C₃H₇ H H 3-F 2-CH₃-4-(F₅—PhO) 206-207 521 i-C₃H₇ H H 3-F 2-CH₃-4-(2-Cl-4- 215-217 CF₃—PhO) 522 i-C₃H₇ H H 3-F 2-CH₃-4-(4-Cl—PhS) 176-178 523 i-C₃H₇ H H 3-F 2-CH₃-4-(5-CF₃-2-Pyi-O) 175-176 524 i-C₃H₇ H H 3-F 2-CH₃-4-(3-Cl- 188-190 5-CF₃-2-Pyi-O) 525 i-C₃H₇ H H 3-F 4-(3-Cl-5-CF₃-2-Pyi-S) 213-215 526 i-C₃H₇ H H 3-F 2-CH₃-4-OP═S(OCH₃)₂ 175-177 527 i-C₃H₇ H H 3-F 2-CF₃-4-OCHF₂ 180-182 528 i-C₃H₇ H H 3-F -3-OCH₂O-4- 197-199 529 i-C₃H₇ H H 4-F 2-CH₃-4-Cl 217-218 530 i-C₃H₇ H H 4-F 2-CH₃-5-Cl 202-203 531 i-C₃H₇ H H 4-F 2-CH₃-4-OCHF₂ 191-193 532 i-C₃H₇ H H 5-F 2-CH₃-4-Cl 197-198 533 i-C₃H₇ H H 5-F 2-CH₃-4-CF₂CF₂CF₃ 213-215 534 i-C₃H₇ H H 5-F 2-CH₃-4-OCHF₂ 181-182 535 i-C₃H₇ H H 6-F 4-CF₂CF₂CF₃ 201-202 536 i-C₃H₇ H H 6-F 4-(CF₂)₃CF₃ 156-158 537 i-C₃H₇ H H 6-F 4-OCF₃ 212-214 538 i-C₃H₇ H H 6-F 4-OCF₂CHFOC₃F₇-n 178-180 539 i-C₃H₇ H H 6-F 4-SCH₂CF₃ 176-178 540 i-C₃H₇ H H 6-F 4-SCF₂CHF₂ 230-232 541 i-C₃H₇ H H 6-F 4-SCF(CF₃)₂ 218-220 542 i-C₃H₇ H H 6-F 4-S(CF₂)₃CF₃ 178-181 543 i-C₃H₇ H H 6-F 2,3-Cl₂ 158-160 544 i-C₃H₇ H H 6-F 2-CH₃-3-Cl 182-184 545 i-C₃H₇ H H 6-F 2-CH₃-4-Cl 204-206 546 i-C₃H₇ H H 6-F 2-CH₃-5-Cl 196-199 547 i-C₃H₇ H H 6-F 2-CH₃-4-I 213-215 548 i-C₃H₇ H H 6-F 2-CH₃-3-F 165-167 549 i-C₃H₇ H H 6-F 2-CH₃-5-F 181-183 550 i-C₃H₇ H H 6-F 2-Cl-4-CF₃ 190-191 551 i-C₃H₇ H H 6-F 2-CH₃-4-CF₂CF₃ 222-223 552 i-C₃H₇ H H 6-F 2-CH₃-4-OCF₂CCl₃ 184-185 553 i-C₃H₇ H H 6-F 2-CH₃-4-OCF₂CCl₂F 214-215 554 i-C₃H₇ H H 6-F 2-CH₃-4-OCF₂CBrF₂ 208-210 555 i-C₃H₇ H H 6-F 2-CH₃-4-CF₂CF₂CF₃ 168-170 556 i-C₃H₇ H H 6-F 2-CH₃-4-CF(CF₃)₂ 255-257 557 i-C₃H₇ H H 6-F 2-CH₃-4-(CF₂)₃CF₃ 157-159 558 i-C₃H₇ H H 6-F 2-CH₃-3-OCHF₂ 177-179 559 i-C₃H₇ H H 6-F 2-CH₃-4-OCHF₂ 176-178 560 i-C₃H₇ H H 6-F 3,5-Cl₂-4-OCHF₂ 198-200 561 i-C₃H₇ H H 6-F 2-Cl-4-CF(CF₃)₂ 241-243 562 i-C₃H₇ H H 6-F 2-Cl-4-OCF₃ 171-172 563 i-C₃H₇ H H 6-F 2-Br-4-OCF₃ 181-182 564 i-C₃H₇ H H 6-F 2-CH₃-4-OCF₃ 193-195 565 i-C₃H₇ H H 6-F 2-CH₃-4-OCBrF₂ 181-183 566 i-C₃H₇ H H 6-F 2-CH₃-4-OCF₂CHF₂ 185-187 567 i-C₃H₇ H H 6-F 2-CH₃-4-OCF₂CHClF 175-176 568 i-C₃H₇ H H 6-F 2-CH₃-4-OCF₂CHFCF₃ 176-178 569 i-C₃H₇ H H 6-F 2-CH₃-4-OCF₂CBrFCF₃ 217-219 570 i-C₃H₇ H H 6-F 2-CH₃-4-OCF₂CHFOCF₃ 183-185 571 i-C₃H₇ H H 6-F 2-CH₃-4-OCHF₂-5-Cl 209-211 572 i-C₃H₇ H H 6-F 2-CH₃-4-(3-CF₃—PhO) 184-185 573 i-C₃H₇ H H 6-F 2-CH₃-4-(F₅—PhO) 227-228 574 i-C₃H₇ H H 6-F 2-CH₃-4-(2-Cl-4-CF₃—PhO) 220-222 575 i-C₃H₇ H H 6-F 2-CH₃-4-(4-Cl—PhS) 190-193 576 i-C₃H₇ H H 6-F 2-CH₃-4-(5-CF₃-2-Pyi-O) 206-207 577 i-C₃H₇ H H 6-F 2-CH₃-4-(3-Cl- 177-179 5-CF₃-2-Pyi-O) 578 i-C₃H₇ H H 6-F 2-CH₃-4-OP═S(OCH₃)₂ 188-190 579 i-C₃H₇ H H 6-F 2-CF₃-4-OCHF₂ 223-225 580 i-C₃H₇ H H 6-F -3-OCH₂O-4- 201-203 581 i-C₃H₇ H H 3,6-F₂ 2-CH₃-4-OCHF₂ 203-204 582 i-C₃H₇ H H 3,6-F₂ 2-CH₃-4-Cl 221-222 583 i-C₃H₇ H H 3,4,5,6-F₄ 2-CH₃-5-Cl 189-191 584 i-C₃H₇ H H 3-NO₂ 2,3-Cl₂ 201-203 585 i-C₃H₇ H H 3-NO₂ H 236-238 586 i-C₃H₇ H H 3-NO₂ 2-Cl 190-192 587 i-C₃H₇ H H 3-NO₂ 3-Cl 227-229 588 i-C₃H₇ H H 3-NO₂ 4-Cl 238-240 589 i-C₃H₇ H H 3-NO₂ 2-Br 170-172 590 i-C₃H₇ H H 3-NO₂ 3-Br 196-198 591 i-C₃H₇ H H 3-NO₂ 4-Br 205-207 592 i-C₃H₇ H H 3-NO₂ 2-F 199-201 593 i-C₃H₇ H H 3-NO₂ 3-F 228-230 594 i-C₃H₇ H H 3-NO₂ 4-F 250-252 595 i-C₃H₇ H H 3-NO₂ 4-I 187-189 596 i-C₃H₇ H H 3-NO₂ 4-NO₂ 201-203 597 i-C₃H₇ H H 3-NO₂ 3-CN 220-222 598 i-C₃H₇ H H 3-NO₂ 4-CN 226-228 599 i-C₃H₇ H H 3-NO₂ 2-CH₃ 227-228 600 i-C₃H₇ H H 3-NO₂ 3-CH₃ 195-197 601 i-C₃H₇ H H 3-NO₂ 4-CH₃ 196-198 602 i-C₃H₇ H H 3-NO₂ 2-C₂H₅ 189-191 603 i-C₃H₇ H H 3-NO₂ 2-C₃H₇-i 190-192 604 i-C₃H₇ H H 3-NO₂ 4-C₃H₇-i 221-223 605 i-C₃H₇ H H 3-NO₂ 4-C₄H₉-n 193-195 606 i-C₃H₇ H H 3-NO₂ 4-CF₃ 192-194 607 i-C₃H₇ H H 3-NO₂ 3-CF₃ 220-222 608 i-C₃H₇ H H 3-NO₂ 2-CF₃ 215-217 609 i-C₃H₇ H H 3-NO₂ 4-CF₂CF₂CF₃ 184-185 610 i-C₃H₇ H H 3-NO₂ 4-CF(CF₃)₂ 243-244 611 i-C₃H₇ H H 3-NO₂ 4-(CF₂)₃CF₃ 220-221 612 i-C₃H₇ H H 3-NO₂ 2-OCH₃ 172-174 613 i-C₃H₇ H H 3-NO₂ 3-OCH₃ 201-203 614 i-C₃H₇ H H 3-NO₂ 4-OCH₃ 221-223 615 i-C₃H₇ H H 3-NO₂ 3-O—C₃H₇-i 198-200 616 i-C₃H₇ H H 3-NO₂ 3-OCHF₂ 188-190 617 i-C₃H₇ H H 3-NO₂ 4-OCHF₂ 222-224 618 i-C₃H₇ H H 3-NO₂ 4-OCF₃ 234-236 619 i-C₃H₇ H H 3-NO₂ 4-OCF₂CHFOC₃F₇-n 138-140 620 i-C₃H₇ H H 3-NO₂ 4-COOCH₃ 192-194 621 i-C₃H₇ H H 3-NO₂ 3-SCH₃ 205-207 622 i-C₃H₇ H H 3-NO₂ 2-SCH₃ 201-203 623 i-C₃H₇ H H 3-NO₂ 3-SCF₃ 203-205 624 i-C₃H₇ H H 3-NO₂ 4-SCH₂CF₃ 155-156 625 i-C₃H₇ H H 3-NO₂ 4-SCHF₂ 183-185 626 i-C₃H₇ H H 3-NO₂ 4-SCF₂CHF₂ 235-237 627 i-C₃H₇ H H 3-NO₂ 4-SCF₂CF₃ 190-192 628 i-C₃H₇ H H 3-NO₂ 4-SCF₂CBrF₂ 228-230 629 i-C₃H₇ H H 3-NO₂ 4-SCF(CF₃)₂ 242-243 630 i-C₃H₇ H H 3-NO₂ 4-S(CF₂)₃CF₃ 229-230 631 i-C₃H₇ H H 3-NO₂ 4-SO(CF₂)₃CF₃ 190-193 632 i-C₃H₇ H H 3-NO₂ 4-O-Ph 228-230 633 i-C₃H₇ H H 3-NO₂ 2,4-Cl₂ 202-204 634 i-C₃H₇ H H 3-NO₂ 2,5-Cl₂ 230-232 635 i-C₃H₇ H H 3-NO₂ 2,6-Cl₂ 210-212 636 i-C₃H₇ H H 3-NO₂ 3,4-Cl₂ 227-229 637 i-C₃H₇ H H 3-NO₂ 3,5-Cl₂ 194-196 638 i-C₃H₇ H H 3-NO₂ 2,3-F₂ 184-186 639 i-C₃H₇ H H 3-NO₂ 2,4-F₂ 210-212 640 i-C₃H₇ H H 3-NO₂ 2,5-F₂ 191-193 641 i-C₃H₇ H H 3-NO₂ 2,6-F₂ 173-175 642 i-C₃H₇ H H 3-NO₂ 3,4-F₂ 241-243 643 i-C₃H₇ H H 3-NO₂ 3-Cl-4-F 203-205 644 i-C₃H₇ H H 3-NO₂ 2,3,4-Cl₃ 203-205 645 i-C₃H₇ H H 3-NO₂ 2,3,4-F₃ 202-204 646 i-C₃H₇ H H 3-NO₂ 2,3,4,5,6-F₅ 192-194 647 i-C₃H₇ H H 3-NO₂ 2,3-(CH₃)₂ 200-202 648 i-C₃H₇ H H 3-NO₂ 2,4-(CH₃)₂ 201-203 649 i-C₃H₇ H H 3-NO₂ 2,5-(CH₃)₂ 221-223 650 i-C₃H₇ H H 3-NO₂ 2,6-(CH₃)₂ 234-236 651 i-C₃H₇ H H 3-NO₂ 3,4-(CH₃)₂ 195-197 652 i-C₃H₇ H H 3-NO₂ 2,4,6-(CH₃)₃ 229-231 653 i-C₃H₇ H H 3-NO₂ 2,6-(C₂H₅)₂ 258-260 654 i-C₃H₇ H H 3-NO₂ 3,5-(CF₃)₂ 225-227 655 i-C₃H₇ H H 3-NO₂ 3-Cl-4-CH₃ 208-210 656 i-C₃H₇ H H 3-NO₂ 2-Cl-4-CH₃ 195-197 657 i-C₃H₇ H H 3-NO₂ 2-F-4-Cl-5-CH₃ 193-195 658 i-C₃H₇ H H 3-NO₂ 3-Cl-4-OCHF₂ 222-224 659 i-C₃H₇ H H 3-NO₂ 3,5-Cl₂-4-OCHF₂ 218-220 660 i-C₃H₇ H H 3-NO₂ 2-Cl-4-CF₃ 217-219 661 i-C₃H₇ H H 3-NO₂ 2-Cl-5-CF₃ 193-195 662 i-C₃H₇ H H 3-NO₂ 2,6-Cl₂-4-CF₃ 226-228 663 i-C₃H₇ H H 3-NO₂ 2-CH₃-3-Cl 198-200 664 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-Cl 235-237 665 i-C₃H₇ H H 3-NO₂ 2-CH₃-5-Cl 218-219 666 i-C₃H₇ H H 3-NO₂ 2-CH₃-6-Cl 248-250 667 i-C₃H₇ H H 3-NO₂ 2-C₂H₅-4-Cl 235-237 668 i-C₃H₇ H H 3-NO₂ 2-CH₃-4,5-Cl₂ 196-198 669 i-C₃H₇ H H 3-NO₂ 2,3-(CH₃)₂-4-Cl 226-228 670 i-C₃H₇ H H 3-NO₂ 2,4-(CH₃)₂-3-Cl 203-205 671 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-Br 214-216 672 i-C₃H₇ H H 3-NO₂ 2-CH₃-5-Br 191-193 673 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-I 227-227 674 i-C₃H₇ H H 3-NO₂ 2-CH₃-3-F 199-201 675 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-F 226-228 676 i-C₃H₇ H H 3-NO₂ 2-CH₃-5-F 213-215 677 i-C₃H₇ H H 3-NO₂ 2-C₂H₅-5-F 191-193 678 i-C₃H₇ H H 3-NO₂ 3-CF₃-4-Cl 215-217 679 i-C₃H₇ H H 3-NO₂ 2-CF₃-4-Cl 208-210 680 i-C₃H₇ H H 3-NO₂ 3-CH₃-4-Br 199-201 681 i-C₃H₇ H H 3-NO₂ 2-CH₃-3-CF₃ 221-222 682 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-CF₃ 236-237 683 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-CF₂CF₃ 218-219 684 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-CF₂CF₂CF₃ 188-189 685 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-CF(CF₃)₂ 248-250 686 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-(CF₂)₃CF₃ 225-226 687 i-C₃H₇ H H 3-NO₂ 2-CH₃-3-OCH₃ 198-200 688 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCH₃ 208-210 689 i-C₃H₇ H H 3-NO₂ 2,3-(CH₃)₂-4-OCH₃ 253-255 690 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-O—C₃H₇-i 233-234 691 i-C₃H₇ H H 3-NO₂ 3-CF₃-5-OCH₃ 214-216 692 i-C₃H₇ H H 3-NO₂ 2-CF₃-4-OCHF₂ 201-203 693 i-C₃H₇ H H 3-NO₂ 3-CF₃-4-OCHF₂ 231-232 694 i-C₃H₇ H H 3-NO₂ 2,4-(CH₃)₂-3-OCH₃ 201-203 695 i-C₃H₇ H H 3-NO₂ 2-CH₃-3-OCHF₂ 200-202 696 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCHF₂ 186-188 697 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCH₂CF₃ 241-243 698 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCF₂CBrF₂ 229-230 699 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCH₂CF₂CHF₂ 199-200 700 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCF₂CBrFCF₃ 224-226 701 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCH₂CHFOCF₃ 208-210 702 i-C₃H₇ H H 3-NO₂ 3-OCH₃-4-OCHF₂ 242-243 703 i-C₃H₇ H H 3-NO₂ 2-Cl-4-CF(CF₃)₂ 198-200 704 i-C₃H₇ H H 3-NO₂ 2-Cl-4-OCF₃ 188-190 705 i-C₃H₇ H H 3-NO₂ 2-Br-4-OCF₃ 202-203 706 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-NO₂ 201-203 707 i-C₃H₇ H H 3-NO₂ 2-Cl-5-NO₂ 193-195 708 i-C₃H₇ H H 3-NO₂ 2-CH₃-5-NO₂ 197-199 709 i-C₃H₇ H H 3-NO₂ 2,3-(CH₃)₂-4-NO₂ 207-209 710 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCF₃ 184-186 711 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCBrF₂ 217-218 712 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCF₂CHF₂ 205-207 713 i-C₃H₇ H H 3-NO₂ 2-CH₃-3-OCF₂CHClF 164-166 714 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCF₂CHClF 192-193 715 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCF₂CCl₂F 212-213 716 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCF₂CHFCF₃ 198-199 717 i-C₃H₇ H H 3-NO₂ 2-CH₃-3-Cl-4-OCHF₂ 236-238 718 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCF₂CHF₂-5-Cl 233-234 719 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-SCH₃ 214-216 720 i-C₃H₇ H H 3-NO₂ 2,3-(CH₃)₂-4-SCH₃ 254-256 721 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-SC₃H₇-i 209-211 722 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-SCHF₂ 225-227 723 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-N(CH₃)₂ 215-217 724 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-(3-CF₃—PhO) 174-175 725 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-(F₅—PhO) 242-244 726 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-(2-Cl- 191-192 4-CF₃—PhO) 727 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-(4-Cl—PhS) 165-167 728 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-(5-CF₃- 216-218 2-Pyi-O) 729 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-(3-Cl- 236-238 5-CF₃-2-Pyi-O) 730 i-C₃H₇ H H 3-NO₂ 4-(3-Cl-5-CF₃- 190-192 2-Pyi-S) 731 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-P═O(OC₂H₅)₂ 128-130 732 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-P═S(OCH₃)₂ 128-130 733 i-C₃H₇ H H 3-NO₂ -3-OCH₂O-4- 229-231 734 i-C₃H₇ H H 3-NO₂ 3-CH₂CH₂CH₂-4 209-211 735 i-C₃H₇ H H 3-NO₂ 2-CH₂CH₂CH₂-3 226-228 736 i-C₃H₇ H H 3-NO₂ 3-N═C(CF₃)—NH-4 162-164 737 i-C₃H₇ H H 3-NO₂ 3-N═C(CF₃)—N(CH₃)-4 186-188 738 i-C₃H₇ H H 5-NO₂ 2-CH₃-5-Cl 226-228 739 i-C₃H₇ H H 6-NO₂ 2-CH₃-5-Cl 247-249 740 i-C₃H₇ H H 6-NO₂ 2-Cl-4-CF₃ Crystals 741 i-C₃H₇ H H 6-NO₂ 2-Cl-4-CF₂CF₂CF₃ 192-193 742 i-C₃H₇ H H 6-NO₂ 2-CH₃-4-CF₃ 239-240 743 i-C₃H₇ H H 6-NO₂ 2-CH₃-4-OCF₂CHFCF₃ 252-253 744 i-C₃H₇ H H 3-CN 2-CH₃-4-Cl 162-164 745 i-C₃H₇ H H 6-CN 2-CH₃-4-Cl Crystals 749 i-C₃H₇ H H 3-CH₃ 4-CCF₃ 180-182 750 i-C₃H₇ H H 3-CH₃ 2-CH₃-4-Cl 169-171 751 i-C₃H₇ H H 3-CH₃ 2-CH₃-4-OCHF₂ 192-193 752 i-C₃H₇ H H 5-CH₃ 2-CH₃-5-Cl 193-195 753 i-C₃H₇ H H 6-C₂H₅ 2-CH₃-4-Cl 180-182 754 i-C₃H₇ H H 3-CF₃ H 202-204 755 i-C₃H₇ H H 3-CF₃ 2-CH₃-5-Cl 196-198 756 i-C₃H₇ H H 3-CF₃ 2-CH₃-3-Cl 216-218 757 i-C₃H₇ H H 3-CF₃ 2,6-(C₂H₅)₂ 238-239 758 i-C₃H₇ H H 3-CF₃ 2-CH₃-4-Cl 207-209 759 i-C₃H₇ H H 3-CF₃ 2-CH₃-4-OCHF₂ 212-213 760 i-C₃H₇ H H 5-CF₃ 2,6-(C₂H₅)₂ 240-241 761 i-C₃H₇ H H 5-CF₃ 2-CH₃-4-Cl 203-205 762 i-C₃H₇ H H 5-CF₃ 3-CF₃-5-OCH₃ 209-210 763 i-C₃H₇ H H 5-CF₃ 2-CH₃-4-OCHF₂ 196-197 764 i-C₃H₇ H H 6-CF₃ H 152-154 765 i-C₃H₇ H H 6-CF₃ 2-CH₃-3-Cl 158-160 766 i-C₃H₇ H H 6-CF₃ 2-CH₃-5-Cl 273-275 767 i-C₃H₇ H H 3-OCH₃ 4-OCF₃ 178-180 768 i-C₃H₇ H H 3-OCH₃ 2-CH₃-4-Br 214-215 769 i-C₃H₇ H H 6-OCH₃ 4-OCF₃ 189-190 770 i-C₃H₇ H H 6-OCH₃ 2-CH₃-5-Cl 155-157 771 i-C₃H₇ H H 6-OCH₃ 2-CH₃-4-Br 195-197 772 i-C₃H₇ H H 3-OCHF₂ 2-CH₃-4-Cl 212-213 773 i-C₃H₇ H H 3-OCHF₂ 2-CH₃-5-Cl 198-200 774 i-C₃H₇ H H 3-OCHF₂ 2-CH₃-4-OCHF₂ 174-175 775 i-C₃H₇ H H 4-OCHF₂ 2-CH₃-5-Cl 215-217 776 i-C₃H₇ H H 5-OCHF₂ 2-CH₃-5-Cl 173-175 777 i-C₃H₇ H H 6-OCHF₂ 2-CH₃-4-Cl 224-226 778 i-C₃H₇ H H 6-OCHF₂ 2-CH₃-5-Cl 191-193 779 i-C₃H₇ H H 6-OCHF₂ 2-CH₃-4-OCHF₂ 199-200 780 i-C₃H₇ H H 3-SCH₃ 2-CH₃-3-Cl 191-193 781 i-C₃H₇ H H 3-SCH₃ 2-CH₃-4-Cl 188-190 782 i-C₃H₇ H H 3-SCH₃ 2-CH₃-4-Br 185-187 783 i-C₃H₇ H H 3-SCH₃ 2-CH₃-4-OCHF₂ 159-161 784 i-C₃H₇ H H 6-SCH₃ 2-CH₃-4-Br 201-202 785 i-C₃H₇ H H 6-SCH₃ 2-CH₃-3-Cl 207-209 786 i-C₃H₇ H H 6-SCH₃ 2-CH₃-4-Cl 204-206 787 i-C₃H₇ H H 6-SCH₃ 2-CH₃-4-OCHF₂ 212-214 788 i-C₃H₇ H H 3-SC₃H₇-i 2-CH₃-4-Cl 183-184 789 i-C₃H₇ H H 6-SC₃H₇-i 2-CH₃-4-Cl 228-229 790 i-C₃H₇ H H 3-SOCH₃ 2-CH₃-4-Br 125-130 791 i-C₃H₇ H H 3-SOCH₃ 2-CH₃-4-OCHF₂ 215-217 792 i-C₃H₇ H H 6-SOCH₃ 2-CH₃-4-Br 203-208 793 i-C₃H₇ H H 3-SOC₃H₇-i 2-CH₃-4-Cl 157-160 794 i-C₃H₇ H H 6-SOC₃H₇-i 2-CH₃-4-Cl 170-173 795 i-C₃H₇ H H 3-SO₂CH₃ 2-CH₃-4-OCHF₂ 211-213 796 i-C₃H₇ H H 3-SO₂C₃H₇-i 2-CH₃-4-Cl 240-242 797 i-C₃H₇ H H 3-SCH₂CF₃ 2-CH₃-4-OCHF₂ 184-186 798 i-C₃H₇ H H 6-SCH₂CF₃ 2-CH₃-4-OCHF₂ 239-241 799 i-C₃H₇ H H 3-SOCH₂CF₃ 2-CH₃-4-OCHF₂ 198-200 800 i-C₃H₇ H H 6-SOCH₂CF₃ 2-CH₃-4-OCHF₂ 238-240 801 i-C₃H₇ H H 6-C≡CH 2-CH₃-4-Cl 253-255 802 i-C₃H₇ H H 6-COOCH₃ 2-CH₃-4-Cl 149-151 803 i-C₃H₇ H H 3-CONHC₃H₇-i 2-CH₃-4-Cl 187-189 804 i-C₃H₇ H H 6-CONHC₃H₇-i 2-CH₃-4-Cl 191-193 807 i-C₃H₇ H H 3-Ph 2-CH₃-4-Cl 228-229 808 i-C₃H₇ H H 6-Pb 4-OCF₃ 213-214 809 i-C₃H₇ H H 6-Ph 2-CH₃-4-Cl 254-256 810 i-C₃H₇ H H 3-O-Ph 2-CH₃-4-OCHF₂ 175-177 811 i-C₃H₇ H H 6-O-Ph 2-CH₃-4-OCHF₂ 194-196 812 i-C₃H₇ H H 3-(4-Cl—PhO) 2-CH₃-4-Br 204-206 813 i-C₃H₇ H H 3-S—Ph 2-CH₃-4-Cl 204-206 814 i-C₃H₇ H H 3-S—Ph 2-CH₃-4-Br 193-194 815 i-C₃H₇ H H 6-S—Ph 2-CH₃-4-Cl 211-213 816 i-C₃H₇ H H 6-S—Ph 2-CH₃-4-Br 193-194 817 i-C₃H₇ H H 3-SO—Ph 2-CH₃-4-Cl 201-203 818 i-C₃H₇ H H 3-SO₂—Ph 2-CH₃-4-Cl 189-191 819 i-C₃H₇ H H 3-CH═CH—CH═CH-4 2-CH₃-4-OCHF₂ 158-160 820 i-C₃H₇ H H 5-CH═CH—CH═CH-6 2-CH₃-4-OCHF₂ 154-155 821 i-C₃H₇ H H 3-CH═CH-CH═CH-4 2-CH₃-5-Cl 156-158 822 i-C₃H₇ H H 4-CH═CH-CH═CH-5 2-CH₃-5-Cl 229-231 823 i-C₃H₇ H H 5-CH═CH-CH═CH-6 2-CH₃-5-Cl 232-234 824 i-C₃H₇ CH₃ H H 4-CF₃ 178-180 825 i-C₃H₇ CH₃ H 3-NO₂ 2-CH₃-4-OCHF₂ 148-149 826 i-C₃H₇ CH₃ H H 2-CH₃-4-Cl 82-83 827 i-C₃H₇ H CH₃ H 2-CH₃-4-Cl 165-166 828 i-C₃H₇ CH₂OCH₃ H H 2-CH₃-4-Cl Oil 829 n-C₄H₉ H H H 4-CF₃ 171-173 830 n-C₄H₉ H H 3-NO₂ 2-CH₃-5-Cl 172-174 831 i-C₄H₉ H H 3-NO₂ 2-CH₃-5-Cl 186-188 832 i-C₄H₉ H H 3-NO₂ 2-CH₃-4-OCHF₂ 192-193 833 i-C₄H₉ H H H 4-CF₃ 149-151 834 i-C₄H₉ CH₃ H 6-NO₂ 2-CH₃-4-OCHF₂ 135-137 835 s-C₄H₉ H H H 4-CF₃ 194-195 836 s-C₄H₉ H H 3-Cl 2-CH₃-4-OCHF₂ 203-205 837 s-C₄H₉ H H 6-Cl 2-CH₃-4-OCHF₂ 213-215 838 s-C₄H₉ H H 3-NO₂ 2-CH₃-5-Cl 205-207 839 s-C₄H₉ H H 3-NO₂ 2-CH₃-4-OCHF₂ 228-229 840 t-C₄H₉ H H H H 237-239 841 t-C₄H₉ H H H 2-CH₃-5-Cl 200-202 842 t-C₄H₉ H H 3-NO₂ 2-CH₃-5-Cl 256-258 843 t-C₄H₉ H H 3-NO₂ 2-CH₃-4-OCHF₂ 172-173 844 CH₂C(CH₃)₃ H H 3-NO₂ 2-CH₃-4-OCHF₂ 226-227 845 CH(C₂H₅)₂ H H 3-NO₂ 2-CH₃-4-OCHF₂ 245-246 846 CH(CH₃)CH(CH₃)₂ H H 3-NO₂ 2-CH₃-4-OCHF₂ 245-247 847 n-C₈H₁₇ H H 3-NO₂ 2-CH₃-5-Cl 164-166 848 c-C₃H₅ H H H 4-CF₃ 195-197 849 c-C₃H₅ H H 3-Cl 2-CH₃-4-OCHF₂ 156-158 850 c-C₃H₅ H H 6-Cl 2-CH₃-4-OCHF₂ 179-181 851 c-C₃H₅ H H 3-NO₂ 2-CH₃-5-Cl 194-196 852 c-C₃H₅ H H 3-NO₂ 2-CH₃-4-OCHF₂ 191-192 853 c-C₄H₇ H H H 2-CH₃-5-Cl 205-207 854 c-C₄H₇ H H 3-NO₂ 2-CH₃-5-Cl 206-208 855 c-C₄H₇ H H 3-NO₂ 2-CH₃-5-F 199-201 856 c-C₅H₉ H H 3-NO₂ 2-CH₃-4-OCHF₂ 219-220 857 c-C₅H₉ H H H 4-CF₃ 208-210 858 c-C₅H₉ H H 3-NO₂ 2-CH₃-5-Cl 200-202 859 c-C₆H₁₁ H H 3-NO₂ 2-CH₃-5-Cl 225-227 860 CH₂-C₃H₅-c H H 3-NO₂ 2-CH₃-5-F 190-192 861 CH₂CH₂Cl H H 3-NO₂ 2-CH₃-5-F 179-181 862 CH₂CH₂F H H 3-NO₂ 2-CH₃-5-F 179-181 863 CH₂CH₂F H H 3-NO₂ 2-CH₃-4-OCHF₂ 190-191 864 CH₂CF₃ H H H 2-CH₃-5-Cl 187-189 865 CH₂CH═CH₂ H H H 4-CF₃ 161-163 866 CH₂CH═CH₂ H H 3-NO₂ 2-CH₃-5-Cl 175-177 867 CH₂CH═CH₂ H H 3-NO₂ 2-CH₃-4-OCHF₂ 194-195 868 CH₂C≡CH H H H 4-CF₃ 185-188 869 CH₂C≡CH H H 3-NO₂ 2-CH₃-5-Cl 191-193 870 CH₂C≡CH H H 3-NO₂ 2-CH₃-4-OCHF₂ 190-191 871 CH₂CH₂OCH₃ H H 3-NO₂ 2-CH₃-5-Cl 165-167 872 CH₂CH₂OCH₃ H H 3-NO₂ 2-CH₃-4-OCHF₂ 165-167 873 CH(CH₃)CH₂OCH₃ H H H 4-CF₃ 252-253 874 CH(CH₃)CH₂OCH₃ H H 3-NO₂ 2-CH₃-4-OCHF₂ 153-155 875 CH₂CH(OC₂H₅)₂ H H 3-NO₂ 2-CH₃-4-OCHF₂ 149-151 876 CH₂—Ph H H H 4-CF₃ 148-15O 877 CH₂—Ph H H 3-NO₂ 2-CH₃-5-Cl 196-198 878 CH(CH₃)—Ph H H 3-NO₂ 2-CH₃-5-Cl 168-170 879 CH(CH₃)—Ph H H 3-NO₂ 2-CH₃-4-OCHF₂ 187-189 880 CH₂CH₂O—(2,4- H H 3-NO₂ 2-CH₃5-Cl 126-128 (CH₃)₂—Ph) 881 —CH₂CH₂CH₂CH₂— H H 4-CF₃ 170-171 882 —CH₂CH₂CH₂CH₂— H 6-NO₂ 2-CH₃-5-Cl 157-159 883 —CH₂CH₂CH₂CH₂— H 6-NO₂ 2-CH₃-4-OCHF₂ 163-165 884 —CH₂CH₂OCH₂CH₂— H H 4-CF₃ 167-168 885 —CH₂CH₂OCH₂CH₂— H 6-NO₂ 2-CH₃-5-Cl 192-194 886 —CH₂CH₂OCH₂CH₂— H 6-NO₂ 2-CH₃-4-OCHF₂ 186-188 887 —CH₂CH(CH₃) H 6-NO₂ 3-CF₃-5-OCH₃ 164-165 OCH(CH₃)CH₂— 888 CH₂—3-Pyi H H 3-NO₂ 2-CH₃-4-Br 180-182 889 i-C₃H₇ H H H 4-CF₂CF₃ 155-157 890 i-C₃H₇ H H 3-NO₂ 4-CF₂CF₃ 223-225 891 i-C₃H₇ H H 3-F 4-CF₂CF₃ 199-201 892 i-C₃H₇ H H 6-F 4-CF₂CF₃ 213-215 893 i-C₃H₇ H H 3-Cl 4-CF₂CF₃ 214-216 894 i-C₃H₇ H H 6-Cl 4-CF₂CF₃ 225-227 895 i-C₃H₇ H H 3-I 4-CF₂CF₃ 208-210 896 i-C₃H₇ H H 6-I 4-CF₂CF₃ 224-226 897 i-C₃H₇ H H H 2-CH₃-4-OSO₂— 135-137 (4-CH₃—Ph) 898 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OSO₂— 208-210 (4-CH₃—Ph) 899 i-C₃H₇ H H 3-Cl 2-CH₃-4-OSO₂- 187-189 (4-CH₃—Ph) 900 i-C₃H₇ H H 6-Cl 2-CH₃-4-OSO₂- 218-220 (4-CH₃—Ph) 901 i-C₃H₇ H H 3-F 2-F-4-O—(4-CF₃-2- 137-139 Cl—Ph) 902 i-C₃H₇ H H 6-F 2-F-4-O—(4-CF₃-2- 155-157 Cl—Ph) 903 i-C₃H₇ H H 3-Cl 2-F-4-O—(4-CF₃-2- 119-121 Cl—Ph) 904 i-C₃H₇ H H 6-Cl 2-F-4-O—(4-CF₃-2- 154-156 Cl—Ph) 905 i-C₃H₇ H H 3-F 2-CH₃-4-SCF₂CF₃ 140-142 906 i-C₃H₇ H H 6-F 2-CH₃-4-SCF₂CF₃ 162-164 907 i-C₃H₇ H H 3-Cl 2-CH₃-4-SCF₂CF₃ 172-173 908 i-C₃H₇ H H 6-Cl 2-CH₃-4-SCF₂CF₃ 193-195 909 i-C₃H₇ H H 3-I 2-CH₃-4-SCF₂CF₃ 207-209 910 i-C₃H₇ H H 6-I 2-CH₃-4-SCF₂CF₃ 196-198 911 i-C₃H₇ H H 3-Cl 4-CH═C(Cl)CF₃ 196.3-208.2 912 i-C₃H₇ H H 6-Cl 4-CH═C(Cl)CF₃ 202.8-209.4 913 i-C₃H₇ H H 3-Cl 4-CH═CBr₂ 209.8-214.8 914 i-C₃H₇ H H 6-Cl 4-CH═CBr₂ 207.7-213.9 915 i-C₃H₇ H H 3-Cl 4-CH═CCl₂   120.1 916 i-C₃H₇ H H 6-Cl 4-CH═CCl₂   199.7 917 i-C₃H₇ H H 3-I 4-CH═C(Cl)CF₃   196.6 918 i-C₃H₇ H H 6-I 4-CH═C(Cl)CF₃   203.3 919 i-C₃H₇ H H 3-I 2-C₂H₅-4-I   195.5 920 i-C₃H₇ H H 6-I 2-C₂H₅-4-I   242.3 921 C₂H₅ H H H 2-C₂H₅-3-Cl-6-C₂H₅ 171-173 922 i-C₃H₇ H H H 2-C₂H₅-3-Cl-6-C₂H₅ 185-186 923 t-C₄H₉ H H H 2-C₂H₅-3-Cl-6-C₂H₅ 166-167 924 i-C₃H₇ H H 3-Cl 2-C₂H₅-3-Cl-6-C₂H₅ 260-261 925 i-C₃H₇ H H 3-I 2-C₂H₅-3-Cl-6-C₂H₅ 269-271 926 t-C₄H₉ H H 3-Cl 2-C₂H₅-3-Cl-6-C₂H₅ 221-222 927 t-C₄H₉ H H H 2-CH₃-4-Cl 216-218 928 t-C₄H₉ H H H 4-CF₃ 220-221 929 t-C₄H₉ H H H 4-OCF₃ 178-179 930 t-C₄H₉ H H H 2-CH₃-4-OCF₃ 184-185 931 t-C₄H₉ H H H 2-CH₃-4-CF₂CF₃ 223-224 932 t-C₄H₉ H H 3-Cl 2-CH₃-4-CF₂CF₃ 219-220 933 t-C₄H₉ H CH₃ H 4-OCF₃ 155-158 934 t-C₄H₉ H H 3-Cl 4-CF₃ 228-229 935 t-C₄H₉ H H 6-Cl 4-CF₃ 253-255 936 t-C₄H₉ H H 3-Cl 4-OCF₃ 268-270 937 t-C₄H₉ H H 3-Cl 2-CH₃-4-Cl 242-244 938 t-C₄H₉ H H 6-Cl 2-CH₃-4-Cl 262-264 939 t-C₄H₉ H H 3-I 4-CF₃ 268-269 940 t-C₄H₉ H H 3-I 4-OCF₃ 263-265 941 t-C₄H₉ H H 3-I 2-CH₃-4-Cl 218-220 942 t-C₄H₉ H H 3-1 2-CH₃-4-CF₂CF₃ 205-207 943 t-C₄H₉ H H 6-I 2-CH₃-4-CF₂CF₃ 216-217 944 t-C₄H₉ H H 3-Cl 2-CH₃-4-OCF₃ 260-262 945 n-C₄H₉ H H 3-I 2-CH₃-4-CF₂CF₃ 173.1-178.5 946 n-C₄H₉ H H 6-I 2-CH₃-4-CF₂CF₃ 181.8-187.7 947 n-C₅H₁₁ H H 3-I 2-CH₃-4-CF₂CF₃ 140.2-151.4 948 n-C₅H₁₁ H H 6-1 2-CH₃-4-CF₂CF₃ 168.7-171.3 949 n-C₆H₁₃ H H 3-I 2-CH₃-4-CF₂CF₃ 135.5-143.9 950 n-C₆H13 H H 6-I 2-CH₃-4-CF₂CF₃ 167.1-169.9 951 i-C₃H₇ H H 3-I 2-C₂H₅-4-I 254.8-273.8 952 i-C₃H₇ H H 3-I 2-n-C₃H₇-4-I   179.7 953 i-C₃H₇ H H 3-CH₃ 2-CH₃-4-CF₂CF₃ 184-186 954 i-C₃H₇ H H 6-CH₃ 2-CH₃-4-CF₂CF₃ 177-179 955 t-C₄H₉ H H 3-CH₃ 2-CH₃-4-CF₂CF₃ 198-200 956 t-C₄H₉ H H 6-CH₃ 2-CH₃-4-CF₂CF₃ 236-237 957 t-C₄H₉ H H 3-I 2-CH₃-4-OCF₃ 208-210 958 t-C₄H₉ H H 6-I 2-CH₃-4-OCF₃ 253-255 959 n-C₃H₇ H H 3-I 2-CH₃-3-Cl 190-192 960 n-C₃H₇ H H 6-I 2-CH₃-3-Cl 159-161 961 n-C₃H₇ H H 6-I 2-C₂H₅-3-Cl-6-C₂H₅ 225-228 962 i-C₃H₇ H H 3-NO₂ 4-OCOCF₃ 185-187 963 i-C₃H₇ H H 3-Cl 4-OCOCF₃ Paste 964 i-C₃H₇ H H 3-I 4-OCOCF₃ Paste 965 i-C₃H₇ H H 3-I 2-i-C₃H₇-4-I   132.5 966 i-C₃H₇ H H 3-I 2-n-C₄H₉-4-I 194.2-198.3 967 i-C₃H₇ H H 3-I 2-CH₃-4-Br-6-CH₃   119.1 968 i-C₃H₇ H H 3-Cl 4-CO₂CH(CF₃)₂ 168-170 969 i-C₃H₇ H H 3-I 4-CO₂CH(CF₃)₂ 193-195 970 i-C₃H₇ H H 3-NO₂ 4-CO₂CH(CF₃)₂ 215-217 971 i-C₃H₇ H H 3-Cl 2-CH₃-4-C≡C- 123-125 (2,4-Cl₂—Ph) 972 i-C₃H₇ H H 3-I 2-CH₃-4-C≡C— 138-140 (2,4-Cl₂—Ph) 973 i-C₃H₇ H H 3-Cl 3-OCF₂CF₂-4 125-128 974 i-C₃H₇ H H 3-I 3-OCF₂CF₂-4 123-126 975 i-C₃H₇ H H H 3-OCF₂CF₂O-4 152-154 976 i-C₃H₇ H H 3-NO₂ 3-OCF₂CF₂O-4 247-248 977 i-C₃H₇ H H 3-Cl 3-OCF₂CF₂O-4 224-226 978 i-C₃H₇ H H H 4-C(CF₃)₂OH 87-89 979 i-C₃H₇ H H 3-NO₂ 4-C(CF₃)₂OH 205-207 980 i-C₃H₇ H H 3-Cl 4-C(CF₃)₂OH 187-189 981 CH₂CH₂OCH₃ H H 3-I 2-CH₃-4-CF₂CF₃ 145.3-151.7 982 CH₂CH₂OCH₃ H H 6-I 2-CH₃-4-CF₂CF₃ 166.7-169.4 983 CH₂CH₂OC₂H₅ H H 3-I 2-CH₃-4-CF₂CF₃ 146.5-150.3 984 CH₂CH₂OC₂H₅ H H 6-I 2-CH₃-4-CF₂CF₃ 157.3-160.4 985 (CH₂)₃OCH₃ H H 3-I 2-CH₃-4-CF₂CF₃ 151.9-155.8 986 (CH₂)₃OCH₃ H H 6-I 2-CH₃-4-CF₂CF₃ 156.5-158.8 987 CH₂CH═CH₂ H H 3-I 2-CH₃-4-CF₂CF₃   157.5 988 CH₂CH═CH₂ H H 6-I 2-CH₃-4-CF₂CF₃ 164.6-171.3 989 CH₂C≡CH H H 3-I 2-CH₃-4-CF₂CF₃ 153.6-158.4 990 CH₂C≡CH H H 6-I 2-CH₃-4-CF₂CF₃ 171.5-178.1 991 c-C₅H₉ H H 3-I 2-CH₃-4-CF₂CF₃   212.9 992 c-C₅H₉ H H 6-I 2-CH₃-4-CF₂CF₃   205.2 993 c-C₆H₁₁ H H 3-I 2-CH₃-4-CF₂CF₃ 219.7-224.3 994 c-C₆H₁₁ H H 6-I 2-CH₃-4-CF₂CF₃ 239.0-244.4 995 i-C₃H₇ H H H 4-SCF₃ 182-184 996 i-C₃H₇ H H 3-NO₂ 4-SCF₃ 228-229 997 i-C₃H₇ H H 3-Cl 4-SCF₃ 229-231 998 i-C₃H₇ H H 3-I 4-SCF₃ 226-227 999 i-C₃H₇ H H H 4-SOCF₃ 175-178 1000 i-C₃H₇ H H 3-NO₂ 4-SOCF₃ 202-205 1001 i-C₃H₇ H H 3-Cl 4-SOCF₃ 242-244 1002 i-C₃H₇ H H 3-I 4-SOCF₃ 229-231 1003 i-C₃H₇ H H 3-i 3-OCF₂CF₂O-4 163-165 1004 i-C₃H₇ H H 3-I 4-C(CF₃)₂OH 227-229 1005 i-C₄H₉ H H 3-I 2-CH₃-4-CF₂CF₃ 200.4-206.8 1006 i-C₄H₉ H H 6-I 2-CH₃-4-CF₂CF₃ 179.2-181.8 1007 s-C₄H₉ H H 3-I 2-CH₃-4-CF₂CF₃ 226.0-230.9 1008 s-C₄H₉ H H 6-I 2-CH₃-4-CF₂CF₃ 216.1-218.0 1009 s-C₅H₁₁ H H 3-I 2-CH₃-4-CF₂CF₃ 215.3-218.2 1010 s-C₅H₁₁ H H 6-I 2-CH₃-4-CF₂CF₃ 191.4-210.5 1011 CH(C₂H₅)₂ H H 3-I 2-CH₃-4-CF₂CF₃ 234.8-236.9 1012 CH(C₂H₅)₂ H H 6-I 2-CH₃-4-CF₂CF₃ 253.7-255.7 1013 CH(C₂H₅)CH₂O H H 3-I 2-CH₃-4-CF₂CF₃ 177 —CH₃ 1014 CH(C₂H₅)CH₂O H H 6-I 2-CH₃-4-CF₂CF₃ 198.3-201.0 —CH₃ 1015 i-C₅H₁₁ H H 3-I 2-CH₃-4-CF₂CF₃ 190.0-192.5 1016 i-C₅H₁₁ H H 6-I 2-CH₃-4-CF₂CF₃   187.8 1017 i-C₃H₇ H H 3-I 2-C₂H₅-4-CF₂CF₃ 232.5-235.8 1018 t-C₄H₉ H H H 2-CH₃-4-OCHF₂ 138-140 1019 t-C₄H₉ H H 3-Cl 2-CH₃-4-OCHF₂ 206-208 1020 t-C₄H₉ H H 3-I 2-CH₃-4-OCHF₂ 204-206 1021 t-C₄H₉ H H H 2-Cl-4-OCF₃ 162-164 1022 t-C₄H₉ H H 3-Cl 2-Cl-4-OCF₃ 189-191 1023 t-C₄H₉ H H 3-I 2-Cl-4-OCF₃ 188-190 1024 c-C₃H₅ H H 3-I 2-CH₃-4-CF₂CF₃ 156.0-165.0 1025 c-C₃H₅ H H 6-I 2-CH₃-4-CF₂CF₃ 173.2-176.4 1026 CH₂CH(CH₃) H H 3-I 2-CH₃-4-CF₂CF₃   148.6 —C₂H₅ 1027 CH₂CH(CH₃) H H 6-I 2-CH₃-4-CF₂CF₃   157.8 —C₂H₅ 1028 CH₂—C—C₆H₁₁ H H 3-I 2-CH₃-4-CF₂CF₃ 186.8-188.7 1029 CH₂(4-t-C₄H₉ H H 3-I 2-CH₃-4-CF₂CF₃ 226.0-231.2 -c-C₆H₁₁) 1030 CH₂(4-t-C₄H₉ H H 6-I 2-CH₃-4-CF₂CF₃   215.4 -c-C₆H₁₁) 1031 CH(CH₃)CH₂O H H 3-I 2-CH₃-4-CF₂CF₃ 187.2-189.9 —CH₃ 1032 CH(CH₃)CH₂O H H 6-I 2-CH₃-4-CF₂CF₃ 169.7-176.1 —CH₃ 1033 CH(CH₃)CH H H 3-I 2-CH₃-4-CF₂CF₃ 208.3-212.7 —(CH₃)₂ 1034 CH(CH₃)CH H H 6-I 2-CH₃-4-CF₂CF₃ 219.3-223.0 —(CH₃)₂ 1035 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-CF₂CF₃   131.3 1036 C₂H₅ C₂H₅ H 6-I 2-CH₃-4-CF₂CF₃ 137 1037 t-C₄H₉ H H H 2-CH₃-4-CF(CF₃)₂ 172-175 1038 t-C₄H₉ H H 3-Cl 2-CH₃-4-CF(CF₃)₂ 241-243 1039 t-C₄H₉ H H 3-I 2-CH₃-4-CF(CF₃)₂ 238-240 1040 CH₂CF₃ H H 3-I 2-CH₃-4-CF₂CF₃ 166.1-175.5 1041 CH₂CF₃ H H 6-I 2-CH₃-4-CF₂CF₃ 184.7-202.5 1042 i-C₃H₇ CH₃ H 3-I 2-CH₃-4-CF₂CF₃   201.4 1043 i-C₄H₉ CH₃ H 3-I 2-CH₃-4-CF₂CF₃ 183.5-189.0 1044 n-C₃H₇ n-C₃H₇ H 3-1 2-CH₃-4-CF₂CF₃ 142.6-145.4 1045 CH₂CH═CH₂ CH₂CH H 3-I 2-CH₃-4-CF₂CF₃ 100.2-105.6 ═CH₂ 1046 CH₂CH₂O CH₂CH₂O H 3-I 2-CH₃-4-CF₂CF₃ 84.0-87.3 —C₂H₅ —C₂H₅ 1047 CH₂CH₂CH₂CH₂ H 3-I 2-CH₃-4-CF₂CF₃ 172.7-177.3 1048 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-CF₂CF₃   119.1 1049 t-C₄H₉ H H H 2-CH₃-4-OCBrF₂ 195-197 1050 t-C₄H₉ H H 3-Cl 2-CH₃-4-OCBrF₂ 198-200 1051 t-C₄H₉ H H 3-I 2-CH₃-4-OCBrF₂ 196-198 1052 t-C₄H₉ H H H 4-C(CF₃)₂OH 123-125 1053 t-C₄H₉ H H 3-Cl 4-C(CF₃)₂OH 185-187 1054 t-C₄H₉ H H 3-I 4-C(CF₃)₂OH 203-205 1055 i-C₃H₇ H H 3-I 2,4-F₂ 236-237 1056 C₂H₅ H H 3-I 2-CH₃-4-OCF₂ 176-178 —CHF₂ 1057 C₂H₅ H H 6-I 2-CH₃-4-OCF₂ 207-209 —CHF₂ 1058 n-C₃H₇ H H 3-I 2-CH₃-4-OCF₂ 185-187 —CHF₂ 1059 n-C₃H₇ H H 6-I 2-CH₃-4-OCF₂ 215-217 —CHF₂ 1060 t-C₄H₉ H H H 2-CH₃-4-OCF₂ 197-198 —CHF₂ 1061 t-C₄H₉ H H 3-Cl 2-CH₃-4-OCF₂ 192-194 —CHF₂ 1062 t-C₄H₉ H H 3-I 2-CH₃-4-OCF₂ 217-218 -CHF₂ 1063 i-C₃H₇ H H 3-Cl 2-CH₃-4-O—(3,5 186-188 -(CH₃O)₂-2-Pyu) 1064 i-C₃H₇ H H 3-I 2-CH₃-4-O—(3,5 201-202 —(CH₃O) 2-2-Pym) 1065 t-C₄H₉ H H H 3-OCF₂CF₂O-4 156-158 1066 t-C₄H₉ H H 3-Cl 3-OCF₂CF₂O-4 240-241 1067 t-C₄H₉ H H 3-I 3-OCF₂CF₂O-4 252-253 1068 CH₃ CH₃ H 3-I 2-CH₃-4-CF₂CF₃   148.7 1069 n-C₃H₇ CH₃ H 3-I 2-CH₃-4-CF₂CF₃   129.3 1070 CH₂CH₂OCH₂CH₂ H 3-I 2-CH₃-4-CF₂CF₃   164.7 1071 i-C₃H₇ i-C₃H₇ H H 2-CH₃-4-CF₂CF₃   169.1 1072 i-C₃H₇ i-C₃H₇ H 6-I 2-CH₃-4-CF₂CF₃   201.2 1073 C₂H₅ H H 3-I 2-CH₃-4-CF(CF₃)₂ 194-195 1074 C₂H₅ H H 6-I 2-CH₃-4-CF(CF₃)₂ 218-220 1075 n-C₃H₇ H H 3-I 2-CH₃-4-CF(CF₃)₂ 188-190 1076 n-C₃H₇ H H 6-I 2-CH₃-4-CF(CF₃)₂ 201-203 1077 i-C₃H₇ H H H 4-SO₂CF₃ 184-186 1078 i-C₃H₇ H H 3-Cl 4-SO₂CF₃ 239-241 1079 i-C₃H₇ H H 3-I 4-SO₂CF₃ 225-227 1080 t-C₄H₉ H H 3-I 4-SO₂CF₃ 230-232 1081 i-C₃H₇ i-C₃H₇ H 3-I 2-CH₃-4-CF₂CF₃ Paste 1082 CH₂CH₂CH₂CH₂CH₂ H 3-I 2-CH₃-4-CF₂CF₃ 140.0-146.8 1083 CH₂CH₂CH(CH₃)CH₂ H 3-I 2-CH₃-4-CF₂CF₃   171.4 —CH₂— 1086 i-C₃H₇ H H H 2-CH₃-4-OCF₂CF₂ 138-140 —Ph 1087 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₂CF₂ 160-162 —Ph 1088 i-C₃H₇ H H 3-I 2-CH₃-4-OCF₂CF₂ 209-211 —Ph 1089 i-C₃H₇ H H 3- 2-CH₃-4-OCF₂CF₂ 190-192 NO₂ —Ph 1090 i-C₃H₇ H H H 2-CH₃-4-SCH₂CH₂ 190-192 —CF═CF₂ 1091 i-C₃H₇ H H H 2-CH₃-4-SOCH₂CH₂ 149-153 —CF═CF₂ 1092 i-C₃H₇ H H H 2-CH₃-4-SO₂CH₂ 183-185 —CH₂CF═CF₂ 1093 i-C₃H₇ H H 3-Cl 2-CH₃-4-SCH₂CH₂ 168-170 —CF═CF₂ 1094 i-C₃H₇ H H 3-Cl 2-CH₃-4-SOCH₂CH₂ 164-167 —CF═CF₂ 1095 i-C₃H₇ H H 3-Cl 2-CH₃-4-SO₂CH₂ 181-183 —CH₂CF═CF₂ 1096 i-C₃H₇ H H 3-I 2-CH₃-4-SCH₂CH₂ 193-195 —CF═CF₂ 1097 i-C₃H₇ H H 3-I 2-CH₃-4-SOCH₂CH₂ 182-186 -CF═CF₂ 1098 i-C₃H₇ H H 3-I 2-CH₃-4-SO₂CH₂ 208-210 —CH₂CF═CF₂ 1099 i-C₃H₇ H H H 3-OCF₂O-4 216-218 1100 i-C₃H₇ H H 3- 3-OCF₂O-4 227-229 NO₂ 1101 i-C₃H₇ H H 3-Cl 3-OCF₂O-4 243-245 1102 i-C₃H₇ H H 3-I 3-OCF₂O-4 229-231 1103 t-C₄H₉ H H H 3-OCF₂O-4 209-211 1104 t-C₄H₉ H H 3-Cl 3-OCF₂O-4 206-208 1105 t-C₄H₉ H H 3-I 3-OCF₂O-4 228-230 1106 i-C₃H₇ H H H 4-SCBrF₂ 175-177 1107 i-C₃H₇ H H H 4-SOCBrF₂ 158-161 1108 i-C₃H₇ H H 3-NO₂ 4-SCBrF₂ 180-182 1109 i-C₃H₇ H H 3-NO₂ 4-SOCBrF₂ 195-198 1110 i-C₃H₇ H H 3-Cl 4-SCBrF₂ 156-158 1111 i-C₃H₇ H H 3-Cl 4-SOCBrF₂ 218-220 1112 i-C₃H₇ H H 3-I 4-SCBrF₂ 206-208 1113 i-C₃H₇ H H 3-I 4-SOCBrF₂ 158-160 1114 t-C₄H₉ H H 3-Cl 4-SCBrF₂ 210-212 1115 t-C₄H₉ H H 3-I 4-SCBrF₂ 219-220 1116 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-CF₂CF₃ 179.8-183.7 1117 CH₂CH₂CH₂ H 3-I 2-CH₃-4-CF₂CF₃   170.7 —CH₂CH₂CH₂ 1118 C₂H₅ C₂H₅ H 3-NO₂ 2-CH₃-4-OCF₃   161.9 1119 C₂H₅ C₂H₅ H 3-NO₂ 2-CH₃-4-CF(CF₃)₂   169.1 1120 CH₃ CH₃ CH₃ 3-I 2-CH₃-4-CF₂CF₃ 141.9-146.6 1121 i-C₃H₇ CH₃ CH₃ 3-I 2-CH₃-4-CF₂CF₃ Paste 1122 C₂H₅ C₂H₅ CH₃ 3-I 2-CH₃-4-CF₂CF₃ Paste 1123 i-C₃H₇ H H H 4-SCF₃ 135-137 1124 i-C₃H₇ H H 3-NO₂ 4-SCF₃ 187-189 1125 i-C₃H₇ H H 3-Cl 4-SCF₃ 192-194 1126 i-C₃H₇ H H 3-I 4-SCF₃ 194-196 1127 t-C₄H₉ H H 3-I 4-SCF₃ 195-197 1128 C₂H₅ C₂H₅ H 3-I 4-SCF₃ 173-175 1129 C₂H₅ C₂H₅ H 3-I 3-OCF₂O-4 128-130 1130 C₂H₅ C₂H₅ H 3-I 4-C(CF₃)₂OH 152-154 1131 C₂H₅ C₂H₅ H 3-NO₂ 2-CH₃-4-OCF₃ 178.7-182.6 1132 C₂H₅ C₂H₅ H 3-NO₂ 2-CH₃-4-OCF₂CHF₂ 160.8-165.0 1133 C₂H₅ C₂H₅ H 3-NO₂ 2-Cl-4-CF₂CF₃ 91.9-95.2 1134 C₂H₅ C₂H₅ H 3-NO₂ 2-F-4-CF₂CF₃ 162.6-166.8 1135 C₂H₅ C₂H₅ H 3-NO₂ 2-CH₃-4-Cl 188.8-190.8 1136 C₂H₅ C₂H₅ H 3-NO₂ 4-OCF₃ 185.7-187.9 1137 C₂H₅ C₂H₅ H 6-NO₂ 2-CH₃-4-OCF₂CHF₂   111.2 1138 C₂H₅ C₂HS H 6-NO₂ 2-CH₃-4-Cl   149.7 1139 C₂H₅ C₂H₅ H 6-NO₂ 4-OCF₃   173.4 1140 CH₂CH(CH₃)CH₂ H 6-I 2-CH₃-4-CF₂CF₃   166.4 —CH(CH₃)CH₂ 1141 t-C₄H₉ H H 3-I 2-CH₃-4-CF₃ 197-198 1142 i-C₃H₇ H H 3-I 3-N═C(CF₂CF₃)O-4 214-216 1143 t-C₄H₉ H H 3-I 3-N═C(CF₂CF₃)O-4 253-254 1144 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-CF₃ 160-161 1145 i-C₃H₇ H H H 3-OCHFCF₂O-4 102-104 1146 i-C₃H₇ H H 3-NO₂ 3-OCHFCF₂O-4 190-192 1147 i-C₃H₇ H H 3-Cl 3-OCHFCF₂O-4 123-125 1148 i-C₃H₇ H H 3-I 3-OCHFCF₂O-4 218-220 1149 t-C₄H₉ H H H 3-OCHFCF₂O-4 165-167 1150 t-C₄H₉ H H 3-I 3-OCHFCF₂O-4 240-241 1151 C₂H₅ C₂H₅ H 3-I 3-OCHFCF₂O-4 193-195 1152 t-C₅H₁₁ H H 3-F 2-CH₃-4-CF₂CF₃   223.3 1153 t-C₅H₁₁ H H 3-F 2-CH₃-4- 222 CF(CF₃)₂ 1154 t-C₅H₁₁ H H 3-F 2-CH₃-4-OCF₃ 193.6-195.8 1155 t-C₅H₁₁ H H 3-F 2-CH₃-4-OCHF₂ 165.5-174.0 1156 n-C₃H₇ n-C₃H₇ H 3-I 2-CH₃-4-OCF₃ 132.2-135.0 1157 n-C₃H₇ n-C₃H₇ H 3-I 2-CH₃-4-OCHF₂ 81.4-87.8 1158 n-C₃H₇ n-C₃H₇ H 3-I 2-CH₃-4-   116.3 OCF₂CHF₂ 1159 i-C₃H₇ C₂H₅ H 3-I 2-CH₃-4-CF₂CF₃   124.4 1160 i-C₃H₇ C₂H₅ H 3-I 4-OCF₃ 137.3-144.1 1161 i-C₃H₇ H H 3-I 3-OCF₂CHFO-4 161-163 1162 i-C₃H₇ H H 3-NO₂ 3-OCF₂CHFO-4 238-240 1163 i-C₃H₇ H H 3-Cl 3-OCF₂CHFO-4 243-245 1164 i-C₃H₇ H H 3-I 3-OCF₂CHFO-4 192-194 1165 t-C₄H₉ H H H 3-OCF₂CHFO-4 205-207 1166 t-C₄H₉ H H 3-I 3-OCF₂CHFO-4 238-240 1167 C₂H₅ C₂H₅ H 3-I 3-OCF₂CHFO-4 195-197 1168 i-C₃H₇ H H 3-I 2-CH₃-4-SOCF₃ 148-152 1169 t-C₄H₉ H H 3-1 2-CH₃-4-SOCF₃ 165-168 1173 i-C₃H₇ H H 3-I 3-N═C(4-CF₃—Ph) 253-255 1174 t-C₄H₉ H H 3-I 3-N═C(4-CF₃—Ph) 251-253 —O-4 1175 C₂H₅ C₂H₅ H 3-I 3-N═C(4-CF₃—Ph) 231-233 —O-4 1176 i-C₃H₇ H H 3-I 3-O—C(2-CF₃—Ph) 242-244 ═N-4 1177 t-C₄H₉ H H 3-I 3-O—C(2-CF₃—Ph) 229-231 ═N-4 1178 C₂H₅ C₂H₅ H 3-I 3-O—C(2-CF₃—Ph) 203-205 ═N-4 1179 C₂H₅ C₂H₅ C₂H₅ 3-I 2-CH₃-4-CF₂CF₃ Paste 1180 i-C₃H₇ H H 3-I 3-O—C(CF₂CF₃) 130-132 ═N-4 1181 t-C₄H₉ H H 3-I 3-O—C(CF₂CF₃) 205-207 ═N-4 1182 C₂H₅ C₂H₅ H 3-I 3-O—C(CF₂CF₃) 188-190 ═N-4 1183 i-C₃H₇ H H 3-CF₃ 2-CH₃-4-OCF₃ 222-224 1184 i-C₃H₇ H H 3-CF₃ 2-CH₃-4-CF₂CF₃ 219-221 1185 C₂H₅ C₂H₅ H 3-CF₃ 2-CH₃-4-OCF₃ 192-194 1186 C₂H₅ C₂H₅ H 3-CF₃ 2-CH₃-4-CF₂CF₃ 218-220 1187 i-C₃H₇ H H 3-Cl 2-F-4-OCF₃ 126-128 1188 i-C₃H₇ H H 3-I 2-F-4-OCF₃ 220-222 1189 t-C₄H₉ H H 3-I 2-F-4-OCF₃ 198-200 1190 C₂H₅ C₂H₅ H 3-I 2-F-4-OCF₃ 129-131 1191 i-C₃H₇ H H 3-OCF₃ 2-CH₃-4-CF₂CF₃ 190-192 1192 t-C₄H₉ H H 3-OCF₃ 2-CH₃-4-CF₂CF₃ 205-207 1193 C₂H₅ C₂H₅ H 3-OCF₃ 2-CH₃-4-CF₂CF₃ 146-148 1202 i-C₃H₇ H H 4-I 2-CH₃-4-CF₂CF₃ 197-199 1203 i-C₃H₇ H H 5-I 2-CH₃-4-CF₂CF₃ 201-203 1204 i-C₃H₇ H H 4-I 2-CH₃-4-OCHF₂ 241-243 1205 i-C₃H₇ H H 5-I 2-CH₃-4-OCHF₂ 214-216 1206 i-C₃H₇ H H 3-CF₃ 2-CH₃-4-OCF₂CHF₂ 195-197 1207 i-C₃H₇ H H 3-CF₃ 2-CH₃-4-CF(CF₃)₂ 227-229 1208 i-C₃H₇ H H H 2-C₂H₅-4-OCF₃ 160-162 1209 i-C₃H₇ H H 3-Cl 2-C₂H₅-4-OCF₃ 205-207 1210 i-C₃H₇ H H 3-I 2-C₂H₅-4-OCF₃ 241-243 1211 t-C₄H₉ H H 3-I 2-C₂H₅-4-OCF₃ 224-225 1212 C₂H₅ C₂H₅ H 3-I 2-C₂H₅-4-OCF₃ 141-143 1221 i-C₃H₇ H H 3,4-Cl₂ 2-CH₃-4-OCF₃ 199-200 1222 i-C₃H₇ H H 3,4-Cl₂ 2-CH₃-4-CF₂CF₃ 208-209 1223 i-C₃H₇ H H 3,4-Cl₂ 2-CH₃-4-CF(CF₃)₂ 228-229 1224 i-C₃H₇ H H 3,5-Cl₂ 2-CH₃-4-OCF₃ 228-230 1225 i-C₃H₇ H H 3,5-Cl₂ 2-CH₃-4-CF₂CF₃ 219-220 1226 i-C₃H₇ H H 3,5-Cl₂ 2-CH₃-4-CF(CF₃)₂ 211-212 1227 i-C₃H₇ H H 3-Cl-4-F 2-CH₃-4-OCF₃ 184-186 1228 i-C₃H₇ H H 3-Cl-4-F 2-CH₃-4-CF₂CF₃ 178-180 1229 i-C₃H₇ H H 3-Cl-4-F 2-CH₃-4-CF(CF₃)₂ 200-201 1230 t-C₄H₉ H H 3-CF₃ 2-CH₃-4-OCF₃ 209-210 1231 t-C₄H₉ H H 3-CF₃ 2-CH₃-4-CF₂CF₃ 210-211 1232 t-C₄H₉ H H 3-CF₃ 2-CH₃-4-CF(CF₃)₂ 242-243 1233 i-C₃H₇ H H 3-OCF₃ 2-CH₃-4-OCF₃ 219-220 1234 t-C₄H₉ H H 3-OCF₃ 2-CH₃-4-OCF₃ 222-223 1235 C₂H₅ C₂H₅ H 3-OCF₃ 2-CH₃-4-OCF₃ 125-126 1236 i-C₃H₇ H H 3-OCF₃ 2-CH₃-4-CF(CF₃)₂ 235-236 1237 t-C₄H₉ H H 3-OCF₃ 2-CH₃-4-CF(CF₃)₂ 220-222 1238 C₂H₅ C₂H₅ H 3-OCF₃ 2-CH₃-4-CF(CF₃)₂ 156-157 1245 i-C₃H₇ H H 3-CN 2-CH₃-4-CF₂CF₃ 168-170 1246 i-C₃H₇ H H 4-I 2-CH₃-4-OCF₃ 238-240 1247 i-C₃H₇ H H 5-I 2-CH₃-4-OCF₃ 205-206 1248 i-C₃H₇ H H 4-I 2-CH₃-4-OCF₂CHF₂ 222-223 1249 i-C₃H₇ H H 5-I 2-CH₃-4-OCF₂CHF₂ 203-204 1250 i-C₃H₇ H H 4-I 2-CH₃-4-CF(CF₃)₂ 215-216 1251 i-C₃H₇ H H 5-I 2-CH₃-4-CF(CF₃)₂ 216-217 1256 i-C₃H₇ H H 3-Cl 2-CH₃-4-CF₂CF₃ 235-236 -4-F 1257 t-C₄H₉ H H 3-Cl 2-CH₃-4-CF₂CF₃ 225-226 -4-F 1258 C₂H₅ C₂H₅ H 3-Cl 2-CH₃-4-CF₂CF₃ 155-156 -4-F 1259 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₃ 229-231 -4-F 1260 t-C₄H₉ H H 3-Cl 2-CH₃-4-OCF₃ 237-238 -4-F 1261 C₂H₅ C₂H₅ H 3-Cl 2-CH₃-4-OCF₃ 140-141 1262 i-C₃H₇ H H 3-Cl 2-CH₃-4- 264-265 -4-F CF(CF₃)₂ 1263 t-C₄H₉ H H 3-Cl 2-CH₃-4- 253-154 -4-F CF(CF₃)₂ 1264 C₂H₅ C₂H₅ H 3-Cl 2-CH₃-4- 158-159 -4-F CF(CF₃)₂ 1266 i-C₃H₇ H H 3,4- 2-CH₃-4- 162-164 Br₂ CF₂CF₃ 1277 i-C₃H₇ H H 4-Cl 2-CH₃-4- 185-186 CF₂CF₃ 1278 t-C₄H₉ H H 4-Cl 2-CH₃-4- 206-207 CF₂CF₃ 1280 C₂H₅ C₂H₅ H 4-Cl 2-CH₃-4- 163-164 CF₂CF₃ 1281 C₂H₅ C₂H₅ H 4-Cl 2-CH₃-4- 193-194 -6-I CF₂CF₃ 1283 i-C₃H₇ H H 3,4-F₂ 2-CH₃-4-OCF₃ 194-195 1284 t-C₄H₉ H H 3,4-F₂ 2-CH₃-4-OCF₃ 216-217 1285 C₂H₅ C₂H₅ H 3,4-F₂ 2-CH₃-4-OCF₃ 156-157 1287 i-C₃H₇ H H 4,5-F₂ 2-CH₃-4-OCF₃ 195-196 1288 t-C₄H₉ H H 4,5-F₂ 2-CH₃-4-OCF₃ 223-224 1290 i-C₃H₇ H H 3-I 2-CH₃-4-OC 226-227 —(CF₂CF₃)═C —(CF₃)₂ 1291 i-C₃H₇ H H 3-Cl 2-CH₃-4-OC 204-205 —(CF₂CF₃)═C —(CF₃)₂ 1292 i-C₃H₇ H H 3-I 2-CH₃-4-OC 198-199 —(OCH₃)═C —(CF₃)₂ 1293 i-C₃H₇ H H 3-Cl 2-CH₃-4-OC 179-180 —(OCH₃)═C —(CF₃)₂ 1294 CH(CH₃)CH₂OH H H H 2-CH₃-4-C₂F₅ 73-74 1295 i-C₃H₇ H H 6-Cl 2-OCH₃-5-Ph 120 1296 i-C₃H₇ H H 3-Cl 2-OCH₃-5-Ph 195 1297 n-C₃H₇ H H 6-Cl 2-OCH₃-5-Ph 200 1298 CH(CH₃)CH₂OH H H 3-Cl 2-CH₃-4-C₂F₅ 195 1299 CH(C₂H₅)CH₂OH H H H 2-CH₃-4-C₂F₅ 78 1300 CH(CH₃)CH₂OH H H 3-I 2-CH₃-4-C₂F₅ 98-99 1301 i-C₃H₇ H H 3-Cl 2-CH₃-4-C≡C 210 —C₄H₉-t 1302 i-C₃H₇ H H 6-Cl 2-CH₃-4-C≡C 205 —C₄H₉-t 1303 n-C₃H₇ H H 3-I 2-CH₃-4-C₂F₅ 200 1304 n-C₃H₇ H H 6-I 2-CH₃-4-C₂F₅ 195 1305 i-C₃H₇ H H 3-I 2-CH₃-4-C≡C 205 —C₄H₉-t 1306 i-C₃H₇ H H 6-I 2-CH₃-4-C≡C- 170 —C₄H₉-t 1307 CH₂—Ph H H 3-Cl 2-CH₃-4-C₂F₅ 175 1308 CH₂—Ph H H 6-Cl 2-CH₃-4-C₂F₅ 175 1309 CH₂—(2-Cl—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 170 1310 CH₂—(2-Cl—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 210 1311 CH₃ H H 3-I 2-CH₃-4-C₂F₅ 190 1312 CH₃ H H 6-I 2-CH₃-4-C₂F₅ 200 1313 C₂H₅ H H 3-I 2-CH₃-4-C₂F₅ 182 1314 C₂H₅ H H 6-I 2-CH₃-4-C₂F₅ 205 1315 CH₂CH(OH)CH₃ H H 3-Cl 2-CH₃-4-C₂F₅ 187 1316 CH(C₂H₅)CH₂OH H H 3-Cl 2-CH₃-4-C₂F₅ 208 1317 C(CH₃)₂CH₂OH H H 3-Cl 2-CH₃-4-C₂F₅ 181-182 1318 CH₂CH(OH)C₂H₅ H H 3-Cl 2-CH₃-4-C₂F₅ 171-172 1319 CH₂CH₂—Ph H H 3-Cl 2-CH₃-4-C₂F₅ 150 1320 CH₂CH₂—Ph H H 6-Cl 2-CH₃-4-C₂F₅ 190 1321 CH(CH₃)—Ph H H 3-Cl 2-CH₃-4-C₂F₅ 160 1322 CH(CH₃)—Ph H H 6-Cl 2-CH₃-4-C₂F₅ 190 1323 i-C₃H₇ H H 3-Cl 2-CH₃-4 220 —CH₂CH₂C(CH₃)₃ 1324 i-C₃H₇ H H 6-Cl 2-CH₃-4 205 —CH₂CH₂C(CH₃) 1325 i-C₃H₇ H H 3-Cl 2-CH₃-4-C≡C-Ph 215 1326 i-C₃H₇ H H 6-Cl 2-CH₃-4-C≡C-Ph 230 1327 O-n-C₃H₇ H H 3-Cl 2-CH₃-4-C₂F₅ 165 1328 O-n-C₃H₇ H H 6-Cl 2-CH₃-4-C₂F₅ 150 1329 O—CH₂CH≡CHCl H H 3-Cl 2-CH₃-4-C₂F₅ 150 (E) 1330 i-C₃H₇ H H 3-Cl 2-CH₃-4-CN 230 1331 (CH₂)₃—Ph H H 3-Cl 2-CH₃-4-C₂F₅ 112 1332 (CH₂)₃—Ph H H 6-Cl 2-CH₃-4-C₂F₅ 105 1333 CH₂(4-Cl—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 198 1334 CH₂(4-Cl—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 156 1335 CH₂(3-Cl—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 168 1336 CH₂(3-Cl—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 177 1337 CH₂(2-CH₃—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 152 1338 CH₂(2-CH₃—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 147 1339 CH₂(3-CH₃—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ Crystals 1340 CH₂(3-CH₃—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 173 1341 CH₂(4-CH₃—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 175 1342 CH₂(4-CH₃—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ Crystals 1343 CH₂(2-CH₃O—Ph) H H 3-Cl 2-CH₃-4-C₂FS Crystals 1344 CH₂(2-CH₃O—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 176 1345 CH₂(3-CH₃O—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 73 1346 CH₂(3-CH₃O—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 86 1347 CH₂(4-CH₃O—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 169 1348 CH₂(4-CH₃O—Ph) H H 6-Cl 2-CH₃-4-C₂FS 168 1349 CH₂(2,4-Cl₂—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 169 1350 CH₂(2,4-Cl₂—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 205 1351 CH₂(3,4-Cl₂—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 179 1352 CH₂(3,4-Cl₂—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 192 1353 CH₂(2,3-Cl₂—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 179 1354 CH₂(2,3-Cl₂—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 208 1355 CH₂-2-Pyi H H 3-Cl 2-CH₃-4-C₂F₅ 143 1356 (CH₂)₂(2-Cl—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 141 1357 (CH₂)₂(2-Cl—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ Paste 1358 (CH₂)₂(3-Cl—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 117 1359 (CH₂)₂(3-Cl—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ Paste 1360 (CH₂)₂(4-Cl—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 118 1361 (CH₂)₂(4-Cl—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 138 1362 CH(CH₃)(2-Cl—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ Paste 1363 CH(CH₃)(2-Cl—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 197 1364 CH(CH₃)(3-Cl—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 100 1365 CH(CH₃)(3-Cl—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ Crystals 1366 CH(CH₃)(4-Cl—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 195 1367 CH(CH₃)(4-Cl—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ Paste 1368 (CH₂)₂O(2-Cl—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 162 1369 (CH₂)₂O(2-Cl—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 160 1370 (CH₂)₂O(3-Cl—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 115 1371 (CH₂)₂O(3-Cl—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 172 1372 (CH₂)₂O(4-Cl—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 185 1373 (CH₂)₂O(4-Cl—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 148 1374 (CH₂)₂O—Ph H H 3-Cl 2-CH₃-4-C₂F₅ 154 1375 (CH₂)₂O—Ph H H 6-Cl 2-CH₃-4-C₂F₅ 183 1376 (CH₂)₂NH—Ph H H 3-Cl 2-CH₃-4-C₂F₅ 104 1377 (CH₂)₂NH—Ph H H 6-Cl 2-CH₃-4-C₂F₅ Paste 1378 CH(CH₃)CH₂OH H H 6-Cl 2-CH₃-4-C₂F₅ 192 1379 CH(Ph)CH₂OH H H H 2-CH₃-4-C₂F₅ 100-101 1380 CH(4-t-C₄H₉—Ph) H H H 2-CH₃-4-C₂F₅ 107-108 —CH₂OH 1381 C(CH₃)₂CH₂OH H H H 2-CH₃-4-C₂F₅ 227 1382 i-C₃H₇ H H 3-Cl 2-F-4-C₂F₅ 190 1383 i-C₃H₇ H H 3-Cl 2-Cl-4-C₂F₅ 180 1384 i-C₃H₇ H H 3-Cl 2-CF₃-4-C₂F₅ 235 1385 i-C₃H₇ H H 3-I 2-F-4-C₂F₅ 190 1386 i-C₃H₇ H H 3-I 2-Cl-4-C₂F₅ 200 1387 i-C₃H₇ H H 3-I 2-CF₃-4-C₂F₅ 255 1388 i-C₃H₇ H H 3-1 2-OCH₃-4-C₂F₅ 152 1389 i-C₃H₇ H H 3-I 2-CH₃-4-CN 215 1390 2-Fur H H 3-Cl 2-CH₃-4-C₂F₅ 178 1391 2-Fur H H 6-Cl 2-CH₃-4-C₂F₅ 149 1392 2-TetFur H H 3-Cl 2-CH₃-4-C₂F₅ 153 1393 2-TetFur H H 6-Cl 2-CH₃-4-C₂F₅ 130 1394 CH₂-4-Pyi H H 3-Cl 2-CH₃-4-C₂F₅  88 1395 CH₂-4-Pyi H H 6-Cl 2-CH₃-4-C₂F₅ Paste 1396 (CH₂)₃OH H H H 2-CH₃-4-C₂F₅ 83-84 1397 (CH₂)₂OH H H H 2-CH₃-4-C₂F₅ 136 1398 CH₂CH(OH)CH₂Ph H H H 2-CH₃-4-C₂F₅ 77-78 1399 (CH₂)₃OH H H 3-Cl 2-CH₃-4-C₂F₅ 188 1400 CH₂—Ph H H 3-I 2-CH₃-4-C₂F₅ 172 1401 CH₂—Ph H H 6-I 2-CH₃-4-C₂F₅ 212 1402 CH₂(2-Cl—Ph) H H 3-I 2-CH₃-4-C₂F₅ 136 1403 CH₂(2-Cl—Ph) H H 6-I 2-CH₃-4-C₂F₅ 214 1404 CH₂(2-CH₃—Ph) H H 3-I 2-CH₃-4-C₂F₅ 100 1405 CH₂(2-CH₃—Ph) H H 6-I 2-CH₃-4-C₂F₅ 185 1406 CH₂—Ph CH₃ H 3-Cl 2-CH₃-4-C₂F₅ Paste 1407 CH₂—Ph CH₂—Ph H 3-Cl 2-CH₃-4-C₂F₅ 136 1408 CH₂—Ph CH₂—Ph H 6-Cl 2-CH₃-4-C₂FS Paste 1409 i-C₃H₇ H H 3-I 2-C₂F₅-4-Br 250 1410 i-C₃H₇ H H 3-I 2-C₂F₅-4-C₂F₅ 245 1411 CH₂C≡CH H H H 2-CH₃-4-C₂F₅ 133-135 1412 CH(4-Ph-Ph)CH₂ H H 3-Cl 2-CH₃-4-C₂F₅ 112 —OH 1414 C(CH₃)₂C≡CH H H H 2-CH₃-4-C₂F₅ 207 1415 C(CH₃)₂CH₂OH H H 6-Cl 2-CH₃-4-C₂F₅ 231 1416 CH(4-Cl—Ph)CH₂ H H 6-Cl 2-CH₃-4-C₂F₅ 225 —OH 1417 C(CH₃)₂—Ph H H 3-Cl 2-CH₃-4-C₂F₅ 190 1418 C(CH₃)₂CH₂—Ph H H 3-Cl 2-CH₃-4-C₂F₅ 192 1419 CH₂-3-Pyi H H 3-Cl 2-CH₃-4-C₂F₅ Paste 1420 CH₂-3-Pyi H H 6-Cl 2-CH₃-4-C₂F₅ Paste 1421 CH₂—Ph H H 3-Cl 2-CH₃-4-OCHF₂ 187 1422 CH₂—Ph H H 6-Cl 2-CH₃-4-OCHF₂ 198 1423 CH₂—(2-Cl—Ph) H H 3-Cl 2-CH₃-4-OCHF₂ 178 1424 CH₂—(2-Cl—Ph) H H 6-Cl 2-CH₃-4-OCHF₂ 192 1425 CH₂—(2-CH₃—Ph) H H 3-Cl 2-CH₃-4-OCHF₂ 183 1426 CH₂—(2-CH₃—Ph) H H 6-Cl 2-CH₃-4-OCHF₂ 192 1427 t-C₄H₉ H H 3-I 2-F-4-C₂F₅ 220 1428 t-C₄H₉ H H 3-I 2-Cl-4-C₂F₅ 187 1429 t-C₄H₉ H H 3-1 2-CF₃-4-C₂F₅ 240 1430 CH₂—Ph H H 3-I 2-CH₃-4-OCHF₂ 176 1431 CH₂—Ph H H 6-I 2-CH₃-4-OCHF₂ 196 1432 CH₂—(2-Cl—Ph) H H 3-I 2-CH₃-4-OCHF₂ 189 1433 CH₂—(2-Cl—Ph) H H 6-I 2-CH₃-4-OCHF₂ 227 1434 CH₂—(2-CH₃—Ph) H H 3-I 2-CH₃-4-OCHF₂ 215 1435 CH₂—(2-CH₃—Ph) H H 6-I 2-CH₃-4-OCHF₂ 209 1436 CH₂—Ph CH₃ H 6-Cl 2-CH₃-4-C₂F₅ Paste 1437 CH₂—Ph CH₃ H 3-Cl 2-CH₃-4-OCHF₂ Paste 1438 CH₂—Ph CH₃ H 3-I 2-CH₃-4-C₂F₅ 175 1439 CH₂—Ph CH₃ H 6-I 2-CH₃-4-C₂F₅ Paste 1440 CH₂—Ph CH₃ H 3-I 2-CH₃-4-OCHF₂ Paste 1441 CH(C₂H₅)CH₂OH H H 6-Cl 2-CH₃-4-C₂F₅ 213 1442 (R)—C*H(Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 105-107 —CH₂OH 1443 (R)—C*H(Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 145-146 —CH₂OH 1445 (S)-C*H(CH₃) H H 3-Cl 2-CH₃-4-C₂F₅ 93-95 —CH₂OH 1446 (S)-C*H(CH₃) H H 6-Cl 2-CH₃-4-C₂F₅ 93-95 —CH₂OH 1447 t-C₄H₉ H H 3-Cl 4-C₂F₅ 275 1448 t-C₄H₉ H H 3-Cl 2-F-4-C₂F₅ 225 1449 t-C₄H₉ H H 3-Cl 2-Cl-4-C₂F₅ 200 1450 n-C₃H₇ H H 3-I 2-CH₃-4-OCHF₂ 181 1451 n-C₃H₇ H H 6-I 2-CH₃-4-OCHF₂ 233 1452 c-C₃H₅ H H 3-I 2-CH₃-4-OCHF₂ 182 1453 c-C₃H₅ H H 6-I 2-CH₃-4-OCHF₂ 231 1454 s-C₄H₉ H H 3-I 2-CH₃-4-OCHF₂ 225 1455 s-C₄H₉ H H 6-I 2-CH₃-4-OCHF₂ 244 1456 CH₂C≡CH H H 3-I 2-CH₃-4-OCHF₂ 196 1457 CH₂—Ph C₂H₅ H 3-Cl 2-CH₃-4-C₂F₅ Paste 1458 (R)—C*H(CH₃) H H 3-Cl 2-CH₃-4-OCHF₂ 136 —Ph 1459 (S)-C*H(CH₃) H H 3-Cl 2-CH₃-4-OCHF₂ 136 —Ph 1460 (R)—C*H(CH₃) H H 3-Cl 2-CH₃-4-C₂F₅ 94-95 —CH₂OH 1461 (R)—C*H(CH₃) H H 6-Cl 2-CH₃-4-C₂F₅ 94-95 —CH₂OH 1464 C(CH₃)₂CH₂OH H H 3-I 2-CH₃-4-C₂F₅ 118 1465 CH(CH₃)CH₂OH H H 6-I 2-CH₃-4-C₂F₅ 130-131 1466 C(CH₃)₂C≡CH H H 3-Cl 2-CHa-4-C₂FS 210-211 1467 C(CH₃)₂C≡CH H H 6-Cl 2-CH₃-4-C₂F₅ 230 1468 CH₂(2-F—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 187 1469 CH₂(2-F—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 165 1470 CH₂—Ph H H 3-F 2-CH₃-4-C₂F₅ 158 1471 CH₂—Ph H H 6-F 2-CH₃-4-C₂F₅ 134 1472 s-C₄H₉ H H 3-I 2-F-4-C₂F₅ 200 1473 s-C₄H₉ H H 3-I 2-Cl-4-C₂F₅ 205 1474 i-C₃H₇ H H 3-I 2-F-4-n-C₃F₇ 165 1475 t-C₄H₉ H H 3-I 2-C₂H₅-4-C₂F₅ 235 1476 CH₂CH(OH)Ph H H 3-Cl 2-CH₃-4-C₂F₅ 108 1477 CH₂CH(OH)Ph H H 6-Cl 2-CH₃-4-C₂F₅ 105 1478 C(CH₃)₂C≡CH H H 3-Cl 2-CH₃-4-C₂F₅ 105 1479 C(CH₃)₂C≡C H H 3-Cl 2-CH₃-4-C₂F₅ 110 -2-Thi 1480 C(CH₃)₂C≡C—Ph H H 6-Cl 2-CH₃-4-C₂F₅ 194 1481 (R)—C*H(CH₃) H H 3-I 2-CH₃-4-C₂F₅ 103-105 —CH₂OH 1482 (S)-C*H(CH₃) H H 3-I 2-CH₃-4-C₂F₅ 103-105 —CH₂OH 1483 (R)—C*H(CH₃) H H 6-I 2-CH₃-4-C₂F₅ 173-174 —CH₂OH 1484 C(CH₃)₂(4-Cl H H 3-Cl 2-CH₃-4-C₂F₅ 218 —Ph) 1485 C(CH₃)₂(3-Cl H H 3-Cl 2-CH₃-4-C₂F₅ 128 —Ph) 1486 CH₂—Ph H H 3-Cl 2-F-4-C₂F₅ 162 1487 CH₂—Ph H H 3-Cl 2-Cl-4-C₂F₅ 153 1488 C₂H₅ H H 3-Cl 2-F-4-C₂F₅ 135 1489 C₂H₅ H H 3-Cl 2-Cl-4-C₂F₅ 125 1490 C₂H₅ H H 3-Cl 2-F-4-n-C₃F₇ 128 1491 n-C₃H₇ H H 3-Cl 2-F-4-C₂F₅ 153 1492 n-C₃H₇ H H 3-Cl 2-Cl-4-C₂F₅ 147 1493 n-C₃H₇ H H 3-Cl 2-F-4-n-C₃F₇ 142 1494 i-C₃H₇ H H 3-Cl 2-F-4-n-C₃F₇ 142 1495 i-C₃H₇ H H 3-Cl 2-C₂H₅-4-C₂F₅ 213 1496 t-C₄H₉ H H 3-Cl 2-F-4-n-C₃F₇ 172 1497 t-C₄H₉ H H 3-Cl 2-C₂H₅-4-C₂F₅ 194 1498 s-C₄H₉ H H 3-Cl 2-F-4-C₂F₅ 209 1499 s-C₄H₉ H H 3-Cl 2-Cl-4-C₂F₅ 194 1500 s-C₄H₉ H H 3-Cl 2-F-4-n-C₃F₇ 182 1501 s-C₄H₉ H H 3-Cl 2-C₂H₅-4-C₂F₅ 212 1502 C₂H₅ H H 3-I 2-F-4-C₂F₅ 135 1503 C₂H₅ H H 3-I 2-Cl-4-C₂F₅ 155 1504 t-C₄H₉ H H 3-I 2-F-4-n-C₃F₇ 180 1505 t-C₄H₉ H H 3-F 2-CH₃-4-C₂F₅ 220 1506 t-C₄H₉ H H 3-F 2-CH₃-4-OCHF₂ 186 1507 t-C₄H₉ H H 3-F 2-F-4-C₂F₅ 214 1508 t-C₄H₉ H H 3-F 2-Cl-4-C₂F₅ 222 1509 t-C₄H₉ H H 3-F 2-F-4-n-C₃F₇ 179 1510 C₂H₅ H H 3-F 2-F-4-C₂F₅ 125 1511 C₂H₅ H H 6-F 2-F-4-C₂F₅ 155 1512 n-C₃H₇ H H 3-F 2-F-4-C₂F₅ 130 1513 n-C₃H₇ H H 6-F 2-F-4-C₂F₅ 170 1514 i-C₃H₇ H H 3-F 2-F-4-C₂F₅ 190 1515 i-C₃H₇ H H 6-F 2-F-4-C₂F₅ 180 1516 i-C₃H₇ H H 3-F 2-Cl-4-C₂F₅ 210 1517 i-C₃H₇ H H 6-F 2-Cl-4-C₂F₅ 160 1518 (S)—C*H(CH₃) H H 6-I 2-CH₃-4-C₂F₅ 173-174 —CH₂OH 1519 C(CH₃)₂CH₂OH H H 3-I 2-CH₃-4-OCF₃ 205 1520 C(CH₃)₂CH₂OH H H 6-I 2-CH₃-4-OCF₃ 248 1521 i-C₃H₇ H H 3-I 2-CH₃-4-(4-CF₃O 247-250 —Ph) 1522 i-C₃H₇ H H 3-I 2-CH₃-4-(4-CF₃ 243-246 —Ph) 1523 CH₂(2-CF₃—Ph) H H 3-Cl 2-CH₃-4-C₂FS 183 1524 n-C₃H₇ H H 3-I 2-F-4-n-C₃F₇ 145 1525 C₂H₆ C₂H₅ H 3-F 2-CH₃-4-C₂F₅ 135 1526 C₂H₅ C₂H₅ H 3-F 2-CH₃-4-i-C₃F₇ 150 1527 C₂H₅ C₂H₅ H 3-F 2-CH₃-4-OCF₃ 125 1528 C₂H₅ C₂H₅ H 3-F 2-CH₃-4-OCHF₂ 110 1529 C₂H₅ C₂H₅ H 3-F 2-CH₃-4-OCF₂CHF₂ 155 1530 C₂H₅ C₂H₅ H 3-F 2-F-4-C₂F₅ 130 1531 C₂H₅ C₂H₅ H 3-F 2-Cl-4-C₂F₅ 110 1532 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-i-C₃F₇ 142 1533 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-OCF₃ 142 1534 C₂H₅ C₂H₅ H 3-I 4-OCF₃ 142 1535 C₂H₅ C₂H₅ H 3-Cl 2-CH₃-4-C₂F₅ 150 1536 C₂H₅ C₂H₅ H 3-Cl 2-CH₃-4-OCF₃ 123 1537 C₂H₅ C₂H₅ H 3-Cl 2-CH₃-4-i-C₃F₇ 147 1538 C₂H₅ C₂H₅ H 3-Cl 2-CH₃-4-OCHF₂  92 1539 C₂H₅ C₂H₅ H 3-Cl 2-CH₃-4-OCF₂CHF₂ 135 1540 C₂H₅ C₂H₅ H 3-Cl 2-Cl-4-C₂F₅ 110 1541 C₂H₅ C₂H₅ H 3-Cl 2-F-4-C₂F₅ 113 1542 C₂H₅ C₂H₅ H 3-Cl 2-CH₃—Cl 142 1543 C₂H₅ C₂H₅ H 3-Cl 2-C₂H₅-4-C₂F₅ 101 1544 C₂H₅ C₂H₅ H 3-Cl 4-OCF₃ 138 1545 C₂H₅ C₂H₅ H 3-Cl 4-CF₃ 188 1546 C₂H₅ C₂H₅ H 3-F 2-CH₃-4-Cl 135 1547 C₂H₅ C₂H₅ H 3-F 4-CF₃ 175 1548 C₂H₅ C₂H₅ H 3-F 4-OCF₃ 155 1549 C₂H₅ C₂H₅ H 3-F 2-C₂H₅-4-C₂F₅ 80 1550 C₂H₅ C₂H₅ H 3-NO₂ 2-CH₃-4-C₂F₅ 185 1551 C₂H₅ C₂H₅ H 6-NO₂ 2-CH₃-4-C₂F₅ 145 1552 t-C₄H₉ H H 3-I 3-CH₃-4-C₂F₅ 215 1553 CH₂—Ph CH₃ CH₃ 3-Cl 2-CH₃-4-C₂F₅ Paste 1554 CH(CH₃)—Ph H CH₃ 3-Cl 2-CH₃-4-C₂F₅ Paste 1555 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-OCHF₂ 138-139 1556 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-OCF₂CHF₂ 136 1557 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-Cl 179 1558 C₂H₅ C₂H₅ H 3-I 4-CF₃ 187 1559 C₂H₅ C₂H₅ H 3-I 2-C₂H₅-4-C₂F₅ 106 1560 C₂H₅ C₂H₅ H 3-I 2-Cl-4-C₂F₅ 103-105 1561 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-C₂F₅ 115 1562 t-C₄H₉ H H 3-I 2-Br-4-C₂F₅ 185 1563 i-C₃H₇ H H 3-I 3-CH₃-4-C₂F₅ 240 1564 i-C₃H₇ H H H 4-O—(2-Pym) 246 1565 C(CH₃)₂ H H 3-I 2-CH₃-4-C₂F₅ 193 —CH₂CH₃ 1566 C(CH₃)₂ H H 3-I 2-CH₃-4-OCF₃ 180 CH₂CH₃ 1567 C(CH₃)₂CH₂CH₃ H H 3-I 178-179 1568 C(CH₃)₂CH₂CH₃ H H 3-I 2-CH₃-4-OCHF₂ 176-177 1569 C(CH₃)₂CH═CH₂ H H 3-Cl 2-CH₃-4-C₂F₅ 223-224 1570 C(CH₃)₂CH≡C H H 3-Cl 2-CH₃-4-C₂F₅ 92-93 —(4-CH₃—Ph) 1571 C(CH₃)₂CH≡C H H 3-Cl 2-CH₃-4-C₂F₅ 96-97 —(2,4-Cl₂—Ph) 1572 C(CH₃)₂CH≡C H H 3-Cl 2-CH₃-4-C₂F₅ 88-89 —(4-CH₃O—Ph) 1573 n-C₃H₇ C₂H₅ H 3-I 2-CH₃-4-C₂F₅  93 1574 n-C₃H₇ C₂H₅ H 3-I 2-CH₃-4-OCF₃ 109 1575 n-C₃H₇ C₂H₅ H 3-I 2-CH₃-4-OCHF₂ 102 1576 CH₂(4-CF₃O—Ph) H H 3-Cl 2-CH₃-4-C₂F₅ 172 1577 CH₂(4-CF₃O—Ph) H H 6-Cl 2-CH₃-4-C₂F₅ 193 1578 CH₂(3-Cl—Ph) CH₃ H 3-Cl 2-CH₃-4-C₂F₅ Paste 1579 CH₂(2-F—Ph) CH₃ H 3-Cl 2-CH₃-4-C₂F₅ 115 1580 i-C₃H₇ H H 3-I 2-Br-4-C₂F₅ 190 1581 n-C₃H₇ C₂H₅ H 3-F 2-CH₃-4-C₂F₅ 120 1582 n-C₃H₇ C₂H₅ H 3-F 4-OCF₃ 115 1583 n-C₃H₇ C₂H₅ H 3-F 4-OCHF₂  85 1584 n-C₃H₇ C₂H₅ H 3-F 2-Cl-4-C₂F₅  75 1585 C(CH₃)₂CH≡C H H 3-Cl 2-CH₃-4-C₂F₅ 102-103 —(4-CF₃—Ph) 1586 C(CH₃)₂CH≡C H H 3-Cl 2-CH₃-4-C₂F₅ 115-117 —(2,6-Cl₂—Ph) 1587 C(CH₃)₂CH≡C H H 3-Cl 2-CH₃-4-C₂F₅ 169 -2-Pyi 1588 C(CH₃)₂CH≡CH H H 3-Cl 2-CH₃-4-OCHF₂ 191-192 1589 C(CH₃)₂CH═CH₂ H H 6-Cl 2-CH₃-4-C₂F₅ 242 1590 C(CH₃)₂CH≡C H H 3-Cl 2-CH₃-4-C₂F₅ 134-135 -3-Pyi 1591 i-C₃H₇ H H H 2-CH₃-4-(2,6 165 -(CH₃O)₂—Ph) 1592 i-C₃H₇ H H H 2-CH₃-4-(3,5 150 -(CH₃O)₂—Ph) 1593 C₂H₅ C₂H₅ H H 2-CH₃-4-(3,5 Paste -(CH₃O)₂—Ph) 1594 i-C₃H₇ H H 3-Cl 2-F-4-(OCF₂O)-5 195 1595 i-C₃H₇ H H 3-I 2-F-4-(OCF₂O)-5 208 1596 t-C₄H₉ H H 3-I 2-F-4-(OCF₂O)-5 202 1597 i-C₃H₇ H H 3-Cl 2-CH₃-4-(OCHFCF₂ 211 —O)-5 1598 i-C₃H₇ H H 3-I 2-CH₃-4-(OCHFCF₂ 212 —O)-5 1599 t-C₄H₉ H H 3-I 2-CH₃-4-(OCHFCF₂ 217 —O)-5 1600 i-C₃H₇ H H 3-I 2-Cl-4-(OCHFCF₂ 210 —O)-5 1601 i-C₃H₇ H H 3-I 2-Cl-4-(OCF₂CHF 214 —O)-5 1602 C(CH₃)₂C≡CH H H 3-Cl 2-CH₃-4-OCF₃ 178-180 1603 C(CH₃)₂CHBr H H 3-Cl 2-CH₃-4-C₂F₅ 130-131 —CH₂Br 1604 C(CH₃)₂CH═CH H H 3-Cl 2-CH₃-4-C₂F₅ 90-93 —Ph(E) 1605 C(CH₃)₂CH₂Br H H 3-I 2-CH₃-4-OCF₃ 139-141 1606 (S)-C*H H H 3-I 2-CH₃-4-C₂F₅ 105-107 —(CH₃)—CH₂Br 1607 (R)—(C*H H H 3-I 2-CH₃-4-C₂F₅ 105-107 —(CH₃)—CH₂Br 1608 i-C₃H₇ H H 3-I 3-Cl-4-C₂F₅ 145 1609 t-C₄H₉ H H 3-I 3-Cl-4-C₂F₅ 260 1610 i-C₃H₇ H H 3-I 2-CH₃-4-C₂F₅-5-CH₃ 210 1611 t-C₄H₉ H H 3-I 2-CH₃-4-C₂F₅-5-CH₃ 215 1612 i-C₃H₇ H H 3-I 2,3-(CH₃)₂-4-C₂F₅ 210 1613 t-C₄H₉ H H 3-I 2,3-(CH₃)₂-4-C₂F₅ 220 1614 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-(4-F-Ph) 130-133 1615 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-(4-Cl—Ph) 173-175 1616 i-C₃H₇ H H H 2-CH₃-4-O—(2-Thz) 149 1617 i-C₃H₇ H H 3-I Mixture of 2-CH₃-4- 235 (4-(2-CH₃-Thz)) and 2-CH₃-5-(4-(2-CH₃- Thz)) (1:1) 1618 i-C₃H₇ H H 3-I 2-CH₃-4-O—(2-Pym) 239 1619 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-(4-CF₃—Ph) 112-115 1620 i-C₃H₇ H H 3-I 4-CF₂CF₂O-5 239 1621 i-C₃H₇ H H 3-Cl 4-CF₂CF₂O-5 243 1622 i-C₃H₇ H H 3-I 2-Cl-4-OCF₂O-5 226 1623 i-C₃H₇ H H 3-Cl 2-Cl-4-OCF₂O-5 223 1624 t-C₄H₉ H H 3-I 2-Cl-4-OCF₂O-5 221 1625 i-C₃H₇ H H 3-I 2-Cl-4-OCF₂CF₂O 241 1626 i-C₃H₇ H H 3-I 2-Cl-3-OCF₂CF₂O-4 219 1627 C(CH₃)₂CH₂Cl H H 3-I 2-CH₃-4-OCF₃ 160 1628 C(CH₃)₂C≡C H H 3-Cl 2-CH₃-4-C₂F₅ 78-80 -3-Thi 1629 C(CH₃)₂C≡CH H H 3-I 2-CH₃-4-C₂F₅ 187-188 1630 i-C₃H₇ H H 3-I 2-CH₃-4-(3,5-(CH₃O)₂ 199 —Ph) 1631 i-C₃H₇ H H H 3-OCH₂O-4 195 1632 i-C₃H₇ H H H 2-F-4-Cl 177 1633 C(CH₃)₂C≡C H H 3-Cl 2-CH₃-4-C₂F₅ 92-93 —(4-CF₃O—Ph) 1634 C(CH₃)₂C≡CH H H 3-I 2-CH₃-4-OCF₃ 188-189 1635 C(CH₃)₂C≡CH H H 3-I 2-CH₃-4-OCHF₂ 175-176 1636 i-C₃H₇ H H 3-I 4-N═(n-C₃F₇)C—O-5 182 1637 i-C₃H₇ H H 3-I 4-O—C(n-C₃F₇)═N-5 250 1638 i-C₃H₇ H H 3-Cl 4-O—C(n-C₃F₇)═N-5 168 1639 t-C₄H₉ H H 3-I 4-O—C(n-C₃F₇)═N-5 248 1640 i-C₃H₇ H H 3-I 2,3-(CH₃)₂-4-C₂F₅ 195 1641 i-C₃H₇ H H 3-I 2-CH₃-4-OC(CF₃)═N-5 229 1642 i-C₃H₇ H H 3-Cl 2-Cl-3-OCF₂CF₂O-4 188 1643 i-C₃H₇ H H 3-Cl 2-Cl-4-OCF₂CF₂O-5 203 1644 t-C₄H₉ H H 3-I 2-Cl-3-OCF₂CF₂O-4 189 1645 t-C₄H₉ H H 3-I 2-Cl-4-OCF₂CF₂O-5 234 1646 C(CH₃)₂CH₂Cl H H 3-I 2-CH₃-4-C₂F₅ 168-169 1647 C(CH₃)₂CH₂Br H H 3-I 2-CH₃-4-C₂F₅ 167-168 1648 C(CH₃)₂C≡C H H 3-I 2-CH₃-4-C₂F₅  90 -Naph 1649 C(CH₃)₂C≡C H H 3-Cl 2-CH₃-4-C₂F₅ 105-106 —(5-Br-2-Pyi) 1650 C(CH₃)₂C≡C H H 3-Cl 2-CH₃-4-C₂F₅ 103-105 —(2,4-F₂—Ph) 1651 (S)-C*H(CH₃) H H 3-Cl 2-CH₃-4-C₂F₅ 135 —CH₂F 1652 (S)-C*H H H 3-Cl 2-CH₃-4-C₂F₅ 193-198 —(CH₃)—CH₂Br 1653 i-C₃H₇ H H 3-1 2-CH₃-4-C₂F₅-5 210 —Cl 1654 t-C₄H₉ H H 3-I 2-CH₃-4-C₂F₅-5 200 —Cl 1655 i-C₃H₇ H H 3-I 2-CH₃-4-C₂FS-5 190 —CH₃ 1656 t-C₄H₉ H H 3-I 2-CH₃-4-C₂F₅-5 195 —CH₃ 1657 i-C₃H₇ H H H 3-(2-CH₃-4-Thz) 211 1658 i-C₃H₇ H H 3-I 3-(2-CF₃-4-Thz) 122 1659 i-C₃H₇ H H 3-I 3-(2-CH₃-4-Oxa) 102 1660 i-C₃H₇ H H 3-I 2-I-4-OCF₂O-5 252 1661 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₂O-5 218 1662 t-C₄H₉ H H 3-I 2-CH₃O-4-C₂F₅ 135 1663 i-C₃H₇ H H 3-I 2-CH₃-4-i-C₃F₇-5-F 235 1664 t-C₄H₉ H H 3-I 2-CH₃-4-i-C₃F₇-5-F 230 1665 i-C₃H₇ H H 3-I 2-CH₃-4-i-C₃F₇-5-Cl 210 1666 i-C₃H₇ H H 3-I 2-CH₃-4-CF₂CF₂O-5 198 1667 i-C₃H₇ H H 3-I 2-CH₃-4-i-C₃F₇ 270 1668 t-C₄H₉ H H 3-I 2-CH₃-4-i-C₃F₇ 290 1669 i-C₃H₇ H H 3-I 2-F-4-i-C₃F₇ 205 1670 t-C₄H₉ H H 3-I 2-F-4-i-C₃F₇ 210 1671 i-C₃H₇ H H 3-I 2-SCH₃-4-i-C₃F₇ 205 1672 t-C₄H₉ H H 3-I 2-SCH₃-4-i-C₃F₇ 205 1673 i-C₃H₇ H H 3-I 2,4-(CH₃)₂-4-i-C₃F₇ 240 1674 t-C₄H₉ H H 3-I 2,4-(CH₃)₂-4-i-C₃F₇ 245 1675 i-C₃H₇ H H 3-I 4-(2-CH₃-4-Thz) 217 1676 i-C₃H₇ H H 3-I 4-(2-CH₃-4-Oxa) 212 1677 i-C₃H₇ H H 3-I 4-(2-i-C₃H₇-4-Thz) 199 1678 i-C₃H₇ H H 3-NO₂ 4-(2-CH₃-4-Thz) 230 1679 i-C₃H₇ H H 3-I 2-Cl-3-OCF₂CHFO-4 188 1680 i-C₃H₇ H H 3-I 2-Cl-3-OCHFCF₂O-4 191 1681 i-C₃H₇ H H 3-I Mixture of 2-Cl-3- 199 OCHFCF₂O-4-5-Cl and 2-Cl-3-OCHFCF₂O-4-6- Cl (1:1) 1682 i-C₃H₇ H H 3-I 2-Cl-3-N═C(CF₃)—O-4 265 1683 t-C₄H₉ H H 3-I 2-Cl-3-N═C(CF₃)—O-4 259 1684 i-C₃H₇ H H 3-I 2-Br-4-OCF₂CHFO-5 185 1685 i-C₃H₇ H H 3-I Mixture of 2,3-Br₂-4- 250 OCF₂CHFO-5; 2,5-Br₂-3- OCHFCF₂O-4; and 2,6- Br₂-3-OCF₂CHFO-4(1:1:1) 1686 i-C₃H₇ H H 3-I Mixture of 2,3-Br₂-4- 228 OCHFCF₂O-5; 2,5-Br₂-3- OCF₂CHFO-4; and 2,6- Br₂-3-OCF₂CHFO-4(1:1:1) 1689 i-C₃H₇ H H 3-I 2,3-(CH₃)₂-4-i-C₃F₇ 270 1690 t-C₄H₉ H H 3-I 2,3-(CH₃)₂-4-i-C₃F₇ 280 1691 i-C₃H₇ H H 3-I 2-i-C₃H₇-4-i-C₃F₇ 240 1692 t-C₄H₉ H H 3-I 2-i-C₃H₇-4-i-C₃F₇ 245 1693 i-C₃H₇ H H 3-I 2-OC₂H_(5-4-i-C) ₃F₇ 195 1694 t-C₄H₉ H H 3-I 2-OC₂H₅-4-i-C₃F₇ 210 1695 i-C₃H₇ H H 3-I 3-F-4-i-C₃F₇ 265 1696 t-C₄H₉ H H 3-I 3-F-4-i-C₃F₇ 285 1697 i-C₃H₇ H H 3-I 3-Cl-4-i-C₃F₇ 295 1698 i-C₃H₇ H H 3-I 2-Br-4-i-C₃F₇-5-CH₃ 240 1699 i-C₃H₇ H H 3-I 2-Br-4-i-C₃F₇ 240 1700 i-C₃H₇ H H 3-I 2-SCH₃-4-C₂F₅ 200 1703 i-C₃H₇ H H 3-I 4-(2-c-C₃H₅-4-Thz) 198 1714 i-C₃H₇ H H 3-I 2-C₂H₅-4-i-C₃F₇ 220 1715 i-C₃H₇ H H 3-I 2-OCH₃-4-I-C₃F₇ 190 1716 i-C₃H₇ H H 3-I 2,6(CH₃)₂-4-i-C₃F₇ 275 1717 i-C₃H₇ H H 3-I 2,6-(CH₃)₂-4-C₂F₅ 250 1722 i-C₃H₇ H H 3-I 2-Cl-4-i-C₃F₇ 220 1723 t-C₄H₉ H H 3-I 2-Cl-4-i-C₃F₇ 210 1726 i-C₃H₇ H H 3-I 2-(CH₂)4-3-4-i-C₃F₇ 260 1727 t-C₄H₉ H H 3-I 2-(CH₂)4-3-4-i-C₃F₇ 272 1732 i-C₃H₇ H H 3-I 2-Cl-3-OCF₂CF₂O-4 245 1733 i-C₃H₇ H H 3-I 2-Cl-3-OCHFCF₂O-4 190 1737 i-C₃H₇ H H 3-I 4-C(CH₃)═NOCH₃ 190 1742 i-C₃H₇ H H 3-I 2-OCF₂O-3 190 1743 i-C₃H₇ H H 3-I 2-OCF₂O-3-6-Cl 213 1744 i-C₃H₇ H H 3-I 2-OCF₂O-3-4-Cl 202 1745 i-C₃H₇ H H 3-I 2-OCF₂O-3-4,6-Cl₂ 228 1746 i-C₃H₇ H H 3-I 2-OCF₂O-3-4-i-C₃F₇ 175 1747 t-C₄H₉ H H 3-I 2-OCF₂O-3-4-Cl 235 1748 t-C₄H₉ H H 3-I 2-OCF₂O-3-4,6-Cl₂ 243 1749 i-C₃H₇ H H 3-I 4-C(CH₃)═NOCH₂—Ph 205 1750 i-C₃H₇ H H 3-I 4-C(CH₃)═NOCH₂ Decomp. —CH═CH₂ 1751 CH₃ CH₃ H H 2-CH₃-4-Cl 149 1752 C₂H₅ C₂H₅ H H 2-CH₃-4-Cl 172 1753 n-C₃H₇ n-C₃H₇ H H 2-CH₃-4-Cl 126 1762 i-C₃H₇ H H 3-I 3-C(i-C₃F₇)═NN Paste —(i-C₃F₇)-4 1763 i-C₃H₇ H H 3-I 4-i-C₃H₇-2-N═CH—S-3 200 1764 i-C₃H₇ H H 3-I 3-S—C(i-C₃H₇)═N-4 218 1765 i-C₃H₇ H H 3-I 4-(2-CF₃-4-Thz) 105 1766 i-C₃H₇ H H 3-I 3-SCH₃-4-i-C₃F₇ 160 1767 i-C₃H₇ H H 3-I 2-Ph-4-i-C₃F₇ 240 1768 i-C₃H₇ H H 3-I 2-OPh-4-i-C₃F₇ 180 1769 i-C₃H₇ H H 3-I 2-OCH₃-4-i-C₃F₇ 265 1770 (CH₂)₂-3-Pyi H H 3-I 2-CH₃-4-i-C₃F₇ Amorphous 1771 (CH₂)₂-3-Pyi H H 6-I 2-CH₃-4-i-C₃F₇ Amorphous 1772 (CH₂)₂-3-Pyi H H 3-I 2-CH₃-4-OCF₃ 169-173 1773 CH(CH₃)-2-Pyi H H 3-I 2-CH₃-4-i-C₃F₇ Amorphous 1774 CH(CH₃)-2-Pyi H H 6-I 2-CH₃-4-i-C₃F₇ Amorphous 1775 CH(CH₃)-2-Pyi H H 3-I 2-CH₃-4-OCF₃ 158-161 1776 CH(CH₃)-2-Pyi H H 6-I 2-CH₃-4-OCF₃ 213-216 1777 CH(CH₃)-2-Pyi H H 3-I 2-CH₃-4-C₂F₅ 149-152 1778 CH(CH₃)-2-Pyi H H 6-I 2-CH₃-4-C₂F₅ 194-196 1780 N(Ph)COCF₃ H H 3-I 2-CH₃-4-C₂F₅ 239-241 1799 CH(CH₃)-2-Fur H H 3-I 2-CH₃-4-i-C₃F₇ 191 1800 CH(CH₃)-2-Thi H H 3-I 2-CH₃-4-i-C₃F₇ 159 1801 i-C₃H₇ H H 3-CF₃ 2-CH₃-4-C₂F₅ 210-212 1802 i-C₃H₇ H H 3-Cl-6- 2-CH₃-4-C₂F₅ 236-237 CF₃S 1803 i-C₃H₇ H H 3-CF₃SO 2-CH₃-4-C₂F₅ 186-187 1804 i-C₃H₇ H H 6-CF₃SO 2-CH₃-4-C₂F₅ 206-208 1805 i-C₃H₇ H H 3-CF₃SO 2-CH₃-4-i-C₃F₇ 211-213 1815 i-C₃H₇ H H 3-I 2-CH₃-4-s-C₄F₉ 190 1816 i-C₃H₇ H H 3-I 2-OH-4-i-C₃F₇ 155 1824 i-C₃H₇ H H 3-I 2-N═C(CF₃)O-3 132 -4-i-C₃F₇ 1825 i-C₃H₇ H H 3-I 2-N═C(CF₃)O-3 145 1826 t-C₄H₉ H H 3-I 2-N═C(CF₃)O-3 110 -4-i-C₃F₇ 1827 t-C₄H₉ H H 3-I 2-N═C(CF₃)O-3 120 1829 (CH₂)₂NH—CO₂C₂H₅ H H 3-I 2-CH₃-4-i-C₃F₇ 155 1830 (CH₂)₂NHCO₂CH₂Ph H H 3-I 2-CH₃-4-C₂F₅ 155 1831 (CH₂)₂CH═CF₂ H H 3-I 2-CH₃-4-C₂F₅ 180 1838 i-C₃H₇ H H H 2-CH₃-4-OCF₂CF₃ 1839 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-OCF₂CF₃ 1840 i-C₃H₇ H H 3-F 2-CH₃-4-OCF₂CF₃ 1841 i-C₃H₇ H H 3-Cl 2-CH₃-4-OCF₂CF₃ 1842 i-C₃H₇ H H 3-Br 2-CH₃-4-OCF₂CF₃ 1843 i-C₃H₇ H H 3-Cl-4-F 2-CH₃-4-OCF₂CF₃ 1844 i-C₃H₇ H H 3,4-Cl₂ 2-CH₃-4-OCF₂CF₃ 1845 i-C₃H₇ H H 3-I 4-OCF₂CF₃ 1846 i-C₃H₇ H H 3-I 2-Cl-4-OCF₂CF₃ 1847 i-C₃H₇ H H 3-I 2-CH₃-4-OCF₂CF₃ 1848 t-C₄H₉ H H 3-I 2-CH₃-4-OCF₂CF₃ 1849 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-OCF₂CF₃ 1850 i-C₃H₇ H H 3-I 2-C₂H₅-4-OCF₂CF₃ 1851 i-C₃H₇ H H H 2-CH₃-4-O-n-C₃F₇ 1852 i-C₃H₇ H H 3-NO₂ 2-CH₃-4-O-n-C₃F₇ 1853 i-C₃H₇ H H 3-F 2-CH₃-4-O-n-C₃F₇ 1854 i-C₃H₇ H H 3-Cl 2-CH₃-4-O-n-C₃F₇ 1855 i-C₃H₇ H H 3-Br 2-CH₃-4-O-n-C₃F₇ 1856 t-C₄H₉ H H 3-Cl-4-F 2-CH₃-4-O-n-C₃F₇ 1857 C₂H₅ C₂H₅ H 3,4-Cl₂ 2-CH₃-4-O-fl-C₃F₇ 1858 i-C₃H₇ H H 3-I 4-O-n-C₃F₇ 1859 i-C₃H₇ H H 3-I 2-Cl-4-O-n-C₃F₇ 1860 i-C₃H₇ H H 3-I 2-CH₃-4-O-n-C₃F₇ 1861 t-C₄H₉ H H 3-I 2-CH₃-4-O-n-C₃F₇ 1862 C₂H₅ C₂H₅ H 3-I 2-CH₃-4-O-n-C₃F₇ 1863 i-C₃H₇ H H 3-I 2-C₂H₅-4-OCF₂CF₃ 1864 i-C₃H₇ H H 3-I 2-CH₃-4-C≡C-t-C₄F₉ 1865 i-C₃H₇ H H 3-I 2-CH₃-4-C≡C—CF₃ 1866 i-C₃H₇ H H 3-I 2-CH₃-4-C≡C-i-C₃F₇ 1867 i-C₃H₇ H H 3-I 2-CH₃-4-CF═CF₂ 1868 i-C₃H₇ H H 3-I 2-CH₃-4-CF═CFCF₃ 1869 i-C₃H₇ H H 3-I 2-CH₃-4-C(CF₃)═CF₂ 1870 i-C₃H₇ H H 3-I 2-CH₃-4-COCH₃ 1871 i-C₃H₇ H H 3-I 2-CH₃-4-COCF₃ 195 1872 i-C₃H₇ H H 3-I 2-CH₃-4-COC₂F₅ 1873 i-C₃H₇ H H 3-I 2-CH₃-4-COCF(CH₃)₂ 1874 i-C₃H₇ H H 3-I 2-CH₃-4-COOCH₃ 217 1875 i-C₃H₇ H H 3-I 2-CH₃-4-COOC₂H₅ 1876 i-C₃H₇ H H 3-I 2-CH₃-4-C(CH₃)═NOCH₃ 218 1877 i-C₃H₇ H H 3-I 2-CH₃-4-C(CH₃)═NOC₂H₅ 1878 i-C₃H₇ H H 3-I 2-CH₃-4-C(CH₃)═NO —CH₂CH═CH₂ 1879 i-C₃H₇ H H 3-I 2-CH₃-4-C(CH₃)═NO —CH₂C≡CH 1880 i-C₃H₇ H H 3-I 2-CH₃-4-C(CH₃)═NOCH₂—Ph 1881 i-C₃H₇ H H 3-I 2-CH₃-4-CH₂OH 1882 i-C₃H₇ H H 3-I 4-CH(OH)CH₃ 1883 i-C₃H₇ H H 3-I 2-CH₃-4-CH(OH)CH₃ 1884 i-C₃H₇ H H 3-I 2-CH₃-4-CH₂ON═C(CH₃)₂ 1885 i-C₃H₇ H H 3-I 2-CH₃-4-CH₂ON═C(Ph) -i-C₃H₇ 1886 i-C₃H₇ H H 3-I 2-OCH₂O-3-4-i-C₃F₇ 1887 i-C₃H₇ H H 3-I 2-OCH₂CH₂O-3-4-i-C₃F₇ 1888 i-C₃H₇ H H 3-I 2-OCF₂CF₂O-3-4-i-C₃F₇ 1889 i-C₃H₇ H H 3-I 2-OCF₂CHFO-3-4-i-C₃F₇ 1890 i-C₃H₇ H H 3-I 2-OCHFCF₂O-3-4-i-C₃F₇ 1891 i-C₃H₇ H H 3-I 2-SCH₂S-3-4-i-C₃F₇ 1892 i-C₃H₇ H H 3-I 2-SCF₂S-3-4-i-C₃F₇ 1893 i-C₃H₇ H H 3-I 2-SCH₂CH₂S-3-4-i-C₃F₇ 1894 i-C₃H₇ H H 3-I 2-SCF₂CF₂S-3-4-i-C₃F₇ 1895 i-C₃H₇ H H 3-I 2-CH₂OCH₂-3-4-i-C₃F₇ 1896 i-C₃H₇ H H 3-I 2-CH₂SCH₂-3-4-i-C₃F₇ 1897 i-C₃H₇ H H 3-I 2-CF₂OCF₂-3-4-i-C₃F₇ 1898 i-C₃H₇ H H 3-I 2-CF₂SCF₂-3-4-i-C₃F₇ 1899 i-C₃H₇ H H 3-Br 2-CH₃-4-i-C₃F₇ 1900 i-C₃H₇ H H 3-Br 2-CH₃-4-i-C₃F₇ -4-Cl 1901 i-C₃H₇ H H 3-I-4-F 2-CH₃-4-i-C₃F₇ 1902 i-C₃H₇ H H 3-I-4-Cl 2-CH₃-4-i-C₃F₇ 1903 i-C₃H₇ H H 3-I-4-CF₃ 2-CH₃-4-i-C₃F₇ 1904 i-C₃H₇ H H 3-I-4-OCH₃ 2-CH₃-4-i-C₃F₇ 1905 i-C₃H₇ H H 3-I-4-Br 2-CH₃-4-i-C₃F₇ 1906 i-C₃H₇ H H 3-Cl-4-CF₃ 2-CH₃-4-i-C₃F₇ 1907 i-C₃H₇ H H 3-CF₃-4-Cl 2-CH₃-4-i-C₃F₇ 1908 i-C₃H₇ H H 3-CF₃-4-F 2-CH₃-4-i-C₃F₇ 1919 i-C₃H₇ H H 3-CF₃-4-OCH₃ 2-CH₃-4-i-C₃F₇ 1910 i-C₃H₇ H H 3-N═CH—CH═CH-4 2-CH₃-4-i-C₃F₇ 1911 i-C₃H₇ H H 3-OCH₂O-4 2-CH₃-4-i-C₃F₇ 1912 i-C₃H₇ H H 3-OCH₂O-4 2-CH₃-4-C₂F₅ 1913 i-C₃H₇ H H 3-OCH₂O-4 2-CH₃-4-OCF₃ 1914 i-C₃H₇ H H 3-OCF₂O-4 2-CH₃-4-i-C₃F₇ 1915 i-C₃H₇ H H 3-OCF₂O-4 2-CH₃-4-C₂F₅ 1916 i-C₃H₇ H H 3-OCF₂O-4 2-CH₃-4-OCF₃ 1917 i-C₃H₇ H H 3-OCH₂CH₂O-4 2-CH₃-4-i-C₃F₇ 1918 i-C₃H₇ H H 3-OCF₂CF₂O-4 2-CH₃-4-i-C₃F₇ 1919 i-C₃H₇ H H 3-OCHFCF₂O-4 2-CH₃-4-i-C₃F₇ 1920 i-C₃H₇ H H 3-OCF₂CHFO-4 2-CH₃-4-i-C₃F₇ 1921 i-C₃H₇ H H 3-OCH₂CH₂-4 2-CH₃-4-i-C₃F₇ 1922 i-C₃H₇ H H 3-CH₂CH₂O-4 2-CH₃-4-i-C₃F₇ 1923 i-C₃H₇ H H 3-OCF₂CF₂-4 2-CH₃-4-i-C₃F₇ 1924 i-C₃H₇ H H 3-CF₂CF₂O-4 2-CH₃-4-i-C₃F₇ 1925 i-C₃H₇ H H 3-SOCH₃ 2-CH₃-4-i-C₃F₇ 1926 i-C₃H₇ H H 3-SO₂CH₃ 2-CH₃-4-i-C₃F₇ 1927 i-C₃H₇ H H 3-CF₃S 2-CH₃-4-i-C₃F₇ 222-223 1928 i-C₃H₇ H H 6-CF₃S 2-CH₃-4-i-C₃F₇ 219-221 1929 t-C₄H₉ H H 3-CF₃S 2-CH₃-4-i-C₃F₇ 231 1930 t-C₄H₉ H H 6-CF₃S 2-CH₃-4-i-C₃F₇ 245-247 1931 t-C₄H₉ H H 3-CF₃SO₂ 2-CH₃-4-i-C₃F₇ 1932 t-C₄H₉ H H 3-CF₃SO₂ 2-CH₃-4-C₂F₅ 1933 t-C₄H₉ H H 3-CF₃SO₂ 2-CH₃-4-OCF₃ 1934 C₂H₅ C₂H₅ H 3-CF₃SO₂ 2-CH₃-4-i-C₃F₇ 1935 C₂H₅ C₂H₅ H 3-CONHCH₃ 2-CH₃-4-i-C₃F₇ 1936 C₂H₅ C₂H₅ H 3-CON(CH₃)₂ 2-CH₃-4-i-C₃F₇ 1937 C₂H₅ C₂H₅ H 3-COCH₃ 2-CH₃-4-i-C₃F₇ 1938 C₂H₅ C₂H₅ H 3-COC₂H₅ 2-CH₃-4-i-C₃F₇ 1939 C₂H₅ C₂H₅ H 3-C(CH₃)═NOCH₃ 2-CH₃-4-i-C₃F₇ 1940 C₂H₅ C₂H₅ H 3-C(CH₃)═NO 2-CH₃-4-i-C₃F₇ —C₂H₅ 1941 i-C₃H₇ H H 3-C≡CH 2-CH₃-4-C₂F₅ 1942 i-C₃H₇ H H 3-C≡CH 2-CH₃-4-i-C₃F₇ 1943 i-C₃H₇ H H 3-C≡C-t-C₄H₉ 2-CH₃-4-C₂F₅ 195-202 1944 i-C₃H₇ H H 3-C≡C-t-C₄H₉ 2-CH₃-4-i-C₃F₇ 1945 i-C₃H₇ H H 3-C≡C—Ph 2-CH₃-4-C₂F₅ 179-183 1946 i-C₃H₇ H H 3-C≡C—Ph 2-CHa-4-i-C₃F₇ 1947 i-C₃H₇ H H 3-C≡C 2-CH₃-4-C₂F₅ —CF₃ 1948 i-C₃H₇ H H 3-C≡C 2-CH₃-4-i-C₃F₇ —CF₃ 1949 i-C₃H₇ H H 3-C₂F₅ 2-CH₃-4-C₂F₅ 1950 t-C₄H₉ H H 3-C₂F₅ 2-CH₃-4-C₂F₅ 1951 C₂H₅ C₂H₅ H 3-C₂F₅ 2-CH₃-4-C₂F₅ 1952 i-C₃H₇ H H 3-C₂F₅ 2-CH₃-4-i-C₃F₇ 1953 t-C₄H₉ H H 3-C₂F₅ 2-CH₃-4-i-C₃F₇ 1954 C₂H₅ C₂H₅ H 3-C₂F₅ 2-CH₃-4-i-C₃F₇ 1955 i-C₃H₇ SN H 3-I 2-CH₃-4-i-C₃F₇ —(n-C₄H₉) 1956 i-C₃H₇ SO₂CH₃ H 3-I 2-CH₃-4-i-C₃F₇ 1957 i-C₃H₇ CN H 3-I 2-CH₃-4-i-C₃F₇ 1958 i-C₃H₇ COOCH₃ H 3-I 2-CH₃-4-i-C₃F₇ 1959 i-C₃H₇ COOC₂H₅ H 3-I 2-CH₃-4-i-C₃F₇ 1960 i-C₃H₇ COCH₃ H 3-I 2-CH₃-4-i-C₃F₇ 1961 i-C₃H₇ COC₂H₅ H 3-I 2-CH₃-4-i-C₃F₇ 1962 i-C₃H₇ CO—Ph H 3-I 2-CH₃-4-i-C₃F₇ 1963 i-C₃H₇ NHCOCH₃ H 3-I 2-CH₃-4-i-C₃F₇ 1964 C₂H₅ C₂H₅ SN(n 3-I 2-CH₃-4-i-C₃F₇ -C₄H₉)₂ 1965 C₂H₅ C₂H₅ SO₂CH₃ 3-I 2-CH₃-4-i-C₃F₇ 1966 C₂H₅ C₂H₅ CN 3-I 2-CH₃-4-i-C₃F₇ 1967 C₂H₅ C₂H₅ COOCH₃ 3-I 2-CH₃-4-i-C₃F₇ 1968 C₂H₅ C₂H₅ COOC₂H₅ 3-I 2-CH₃-4-i-C₃F₇ 1969 C₂H₅ C₂H₅ COCH₃ 3-I 2-CH₃-4-i-C₃F₇ 1970 C₂H₅ C₂H₅ COC₂H₅ 3-I 2-CH₃-4-i-C₃F₇ Amorphous 1971 C₂H₅ C₂H₅ COPh 3-I 2-CH₃-4-i-C₃F₇ 1972 C₂H₅ C₂H₅ NHCOCH₃ 3-I 2-CH₃-4-i-C₃F₇ 1973 (CH₂)₂COO H H 3-I 2-CH₃-4-i-C₃F₇ —CH₃ 1974 (CH₂)₂COO H H 3-I 2-CH₃-4-C₂F₅ —CH₃ 1975 (CH₂)₂COO H H 3-I 2-CH₃-4-i-C₃F₇   133.2 —C₂H₅ 1976 (CH₂)₂COO H H 3-I 2-CH₃-4-C₂F₅ —C₂H₅ 1977 (CH₂)₂COO H H 6-I 2-CH₃-4-C₂F₅   163.5 —C₂H₅ 1978 CH(CH₃)CH₂ H H 3-I 2-CH₃-4-i-C₃F₇ —COOCH₃ 1979 CH(CH₃)CH₂COOC₂H₅ H H 3-I 2-CH₃-4-i-C₃F₇ 1980 CH(CH₃)CH₂COO-i- H H 3-I 2-CH₃-4-i-C₃F₇ C₃H₇ 1981 (CH₂)₂CONHCH₃ H H 3-I 2-CH₃-4-i-C₃F₇ 1982 (CH₂)₂CONHC₂H₅ H H 3-I 2-CH₃-4-i-C₃F₇ 1983 CH(CH₃)CH₂CONHCH₃ H H 3-I 2-CH₃-4-i-C₃F₇ 1984 CH(CH₃)CH₂CONHC₂H₅ H H 3-I 2-CH₃-4-i-C₃F₇ 1985 CH(CH₃)CH₂CONH-i- H H 3-I 2-CH₃-4-i-C₃F₇ C₃H₇ 1986 CH(CH₃)CH₂CON H H 3-I 2-CH₃-4-i-C₃F₇ —(CH₃)₂ 1987 CH(CH₃)CH₂CON H H 3-I 2-CH₃-4-i-C₃F₇ —(C₂H₅)₂ 1988 (CH₂)₂NHCOOCH₃ H H 3-I 2-CH₃-4-C₂F₅ 1989 (CH₂)₂NHCOOCH₃ H H 3-I 2-CH₃-4-i-C₃F₇ 1990 (CH₂)₂NHCOOC₂H₅ H H 3-I 2-CH₃-4-C₂F₅ 145 1991 (CH₂)₂NHCOOC₂H₅ H H 3-I 2-CH₃-4-OCF₃ 210 1992 CH(CH₃)CH₂NHCOOCH₃ H H 3-I 2-CH₃-4-i-C₃F₇ 1993 CH(CH₃)CH₂NHCOO H H 3-I 2-CH₃-4-i-C₃F₇ —C₂H₅ 1994 (CH₂)₂P(CH₃)₂ H H 3-I 2-CH₃-4-i-C₃F₇ 1995 CH(CH₃)P(C₂H₅)₂ H H 3-I 2-CH₃-4-i-C₃F₇ 1996 (CH₂)₂P(Ph)₂ H H 3-I 2-CH₃-4-i-C₃F₇ 1997 CH(CH₃)CH₂P(CH₃)₂ H H 3-I 2-CH₃-4-i-C₃F₇ 1998 CH(CH₃)CH₂P(C₂H₅)₂ H H 3-I 2-CH₃-4-i-C₃F₇ 1999 CH(CH₃)CH₂P(Ph)₂ H H 3-I 2-CH₃-4-i-C₃F₇ 2000 CH(CH₃)(CH₂)₂P H H 3-I 2-CH₃-4-i-C₃F₇ —(CH₃)₂ 2001 CH(CH₃)(CH₂)₃P H H 3-I 2-CH₃-4-i-C₃F₇ —(CH₃)₂ 2002 (CH₂)₂PO(CH₃)₂ H H 3-I 2-CH₃-4-i-C₃F₇ 2003 (CH₂)₂PO(OC₂H₅)₂ H H 3-I 2-CH₃-4-i-C₃F₇ Amorphous 2004 CH(CH₃)CH₂PO(OCH₃)₂ H H 3-I 2-CH₃-4-i-C₃F₇ 2005 (CH₂)₂OPO(OCH₃)₂ H H 3-I 2-CH₃-4-i-C₃F₇ 2006 CH(CH₃)CH₂PS(OCH₃)₂ H H 3-I 2-CH₃-4-i-C₃F₇ 2007 CH(CH₃)CH₂PS H H 3-I 2-CH₃-4-i-C₃F₇ —(OC₂H₅)₂ 2008 (CH₂)₂OPO(OC₂H₅)₂ H H 3-I 2-CH₃-4-i-C₃F₇ 2009 CH(CH₃)CH₂OPO H H 3-I 2-CH₃-4-i-C₃F₇ —(OCH₃)₂ 2010 CH(CH₃)CH₂OPO H H 3-I 2-CH₃-4-i-C₃F₇ —(OC₂H₅)₂ 2011 (CH₂)₂OPS(OCH₃)₂ H H 3-I 2-CH₃-4-i-C₃F₇ 2012 (CH₂)₂OPS(OC₂H₅)₂ H H 3-I 2-CH₃-4-i-C₃F₇ 2013 CH(CH₃)CH₂OPS H H 3-I 2-CH₃-4-i-C₃F₇ —(OCH₃)₂ 2014 CH(CH₃)CH₂OPS H H 3-I 2-CH₃-4-i-C₃F₇ —(OC₂H₅)₂ 2015 CH(CH₃)-2-Pyi-N H H 3-I 2-CH₃-4-C₂F₅ 198-205 -Oxide 2016 CH(CH₃)-2-Pyi-N H H 3-I 2-CH₃-4-i-C₃F₇ 208-210 -Oxide 2017 i-C₃H₇ H H 3-I 2-CH₃-4-C(CF₃) ═NOCH₃ 2018 i-C₃H₇ H H 3-I 2-CH₃-4-C(CF₃) ═NOCH₂Ph 2019 i-C₃H₇ H H 3-I 2-NCHCHCHCH-3 180 -4-i-C₃F₇ 2020 i-C₃H₇ H H 3-I 2-n-C₃H₇-4-i 225 -C₃F₇ 2021 i-C₃H₇ H H 3-I 2-O—(2-Pyi)-4 158.3-159.8 -i-C₃F₇

The abbreviations in Table 1 stand for the following substituents:

Ph: phenyl group,

c-: alicyclic hydrocarbon group,

Pyi: pyridyl group,

Pym: pyrimidinyl group,

Fur: furyl group,

TetFur: tetrahydrofuryl group,

Thi: thienyl group,

Thz: thiazolyl group,

Naph: naphthyl group,

Oxa: oxazolyl group,

C*: asymmetric carbon atom

TABLE 2 Physical Properties (melting No R¹ R² R³ Xn Ym Z¹ Z² point: ° C. S-1 i-C₃H₇ H H 3-Cl 2-CH₃-4-CF₂CF₃ S 0 162-164 S-2 t-C₄H₉ H H 3-Cl 2-CH₃-4-CF₂CF₃ S 0 141-143 S-3 c-C₃H₅ H H 3-Cl 2-CH₃-4-CF₂CF₃ S 0 138-139 S-4 C₂H₅ C₂H₅ H 3-Cl 2-CH₃-4-CF₂CF₃ S 0 184-186 S-5 i-C₃H₇ H H H 2-CH₃-4-Cl S 0 168-170 S-6 i-C₃H₇ H H H 2-CH₃-4-Cl 0 S S-7 i-C₃H₇ H H 3-I 2-CH₃-4-i-C₃H₇ 0 S S-8 i-C₃H₇ H H H 2-CH₃-4-i-C₃H₇ S S S-9 i-C₃H₇ H H 3-I 2-CH₃-4-i-C₃H₇ S S

The ¹H-NMR data of the compounds obtained as paste (physical properties) are given in Table 3 below.

TABLE 3 No. ¹H-NMR[CDCl₃/TMS, δ values (ppm)] 1122 1.2-1.4(m.6H), 2.4-2.5(m.3H), 3.1-3.9(m.7H), 6.6-7.9(m.6H) 1218 1.3(d.3H), 2.3(s.3H), 2.9-3.2(m.2H), 4.4(m.1H), 6.2(d.1H), 7.1-7.5(m.3H), 7.8(d.1H), 8.0(d.1H), 8.4(d.1H), 8.5(s.1H).

The fluorine-containing aniline compound of the general formula (ST-I) of the present invention is useful as an intermediate of a medicine, agrochemical, chemical product etc., particularly, is useful as a starting material of the phthalic acid diamide derivative of the general formula (I) of the present invention. That is, the fluorine-containing aniline compound of the general formula (ST-I) is useful as an aniline of the general formula (IV) in the Production processes 1, 3, 5 and 6 as illustrated above. The fluorine-containing aniline compound of the general formula (ST-I) of the present invention can be produced, for example, by any of the following production processes.

wherein each of X^(a), X^(b) and X^(c) is a hydrogen atom, an iodine atom or a bromine atom, provided that at least one of X^(a), X^(b) and X^(c) is not a hydrogen atom, and R^(a), R^(b), R^(c) and R^(d) are as defined above.

A fluorine-containing aniline compound of the general formula (ST-I) can be produced by reacting an aniline derivative of the general formula (ST-II) with a perfluoroalkyl iodide of the general formula (ST-III), general formula (ST-IV) or general formula (ST-V) in the presence of activated copper powder and an inert solvent.

Usually, the amount of each of the perfluoroalkyl iodide of the general formula (ST-III), (ST-IV) or (ST-V) and the activated copper powder used may be properly chosen in the range of 1 to 5 times the amount of the aniline derivative of the general formula (ST-II).

As the inert solvent used in the reaction, any solvent may be used so long as it does not remarkably inhibit the progress of the reaction. There can be used, for example, aprotic polar solvents such as N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), etc. The reaction temperature may be properly chosen in the range of room temperature to 200° C.

After completion of the reaction, the desired compound is isolated from the reaction mixture containing the desired compound by a conventional method and can, if necessary, be purified by silica gel chromatography, distillation, recrystallization, etc.

The reaction can be carried out by the method described in Bull. Chem. Soc. Jpn., 65, 2141-2144 (1992).

wherein R^(a), R^(b), R^(c), R^(d), X^(a), X^(b) and X^(c) are as defined above, and R^(e) is a protecting group such as an acyl group.

A fluorine-containing aniline compound of the general formula (ST-I) can be produced by reacting an acylaniline derivative of the general formula (ST-VI) with a perfluoroalkyl iodide of the general formula (ST-III), general formula (ST-IV) or general formula (ST-V) in the presence of activated copper powder and an inert solvent to obtain an acylaniline derivative of the general formula (ST-VII), and deacylating the acylaniline derivative (ST-VII) after or without isolation.

{circle around (1)} General Formula (ST-VI)→General Formula (ST-VII)

This reaction can be carried out according to production process 8.

{circle around (2)} General Formula (ST-VII)→General Formula (ST-I)

This reaction is usually carried out under acidic conditions. In the reaction, for example, an aqueous mineral acid solution such as a 5 to 35% aqueous hydrochloric acid solution is used as an acid. If necessary, there may be used together therewith alcohols such as methanol, ethanol, etc., and inert solvents such as tetrahydrofuran (THF), acetonitrile, etc. The reaction temperature may be chosen in the range of room temperature to the boiling point of the solvent used. The desired compound can be produced by carrying out the similar workup as in production process 8.

wherein R^(a), R^(b), R^(c), R^(d), X^(a), X^(b) and X^(c) are as defined above.

A fluorine-containing aniline compound of the general formula (ST-I) can be produced by reacting a nitrobenzene derivative of the general formula (ST-VIII) with a perfluoroalkyl iodide of the general formula (ST-III), general formula (ST-IV) or general formula (ST-V) in the presence of activated copper powder and an inert solvent to obtain a nitrobenzene derivative of the general formula (ST-IX), and reducing the nitrobenzene derivative (ST-IX) after or without isolation.

{circle around (1)} General Formula (ST-VIII)→General Formula (ST-IX)

This reaction can be carried out according to production process 8.

{circle around (2)} General Formula (ST-IX)→General Formula (ST-I)

Usually, the desired compound can be produced by subjecting the nitrobenzene derivative (ST-IX) to catalytic hydrogenation in an alcohol solvent in the presence of a catalyst such as 5% palladium carbon (proportion: 1 to 5% by weight), or reducing the nitro-benzene derivative (ST-IX) with an aqueous hydrochloric acid solution containing stannous chloride, in a solvent such as ethanol.

The reaction {circle around (2)} can be carried out according to the method described in Journal of Chemical Society of Japan, 1973, 2351.

Typical examples of the fluorine-containing aniline compound of the general formula (ST-I) of the present invention are given in Table 4 but they are not intended in any way to limit the scope of the present invention.

General Formula (ST-I):

TABLE 4 Physical property or No. R^(a) R^(b) R^(c) R^(d) ¹H-NMR (δ, ppm) ST-1 CH₃ H H C₂F₅ 2.21(s,3H), 3.84(br, 2H), 6.86(s,1H), 6.91(d,1H), 7.15(d, 1H). ST-2 CH₃ H H i-C₃F₇ ST-3 CH₃ H C₂F₅ H b.p.  95-105° C./ 10 mmHg ST-4 CH₃ H i-C₃F₇ H b.p. 100-110° C./ 10 mmHg ST-5 CH₃ H n-C₃F₇ H 2.20(s,3H), 3.9(br, 2H), 6.70(d,1H), 7.22-7.27(m,2H). ST-6 CH₃ H n-C₄F₉ H 2.19(s,3H), 4.2(br, 2H), 6.70(d,1H), 7.20-7.26(m,2H). ST-7 CH₃ H CF H (CF₃)— C₂F₅ ST-8 CH₃ C₂F₅ H H 2.22(s,3H), 3.83(br, 2H), 6.86(d,1H), 6.99(d,1H), 7.12(t, 1H). ST-9 CH₃ i-C₃F₇ H H ST-10 F H i-C₃F₇ H ST-11 Cl H C₂F₅ H 4.4(br,2H), 6.8(d, 1H), 7.27(dd,1H), 7.47(d,1H). ST-12 Cl H i-C₃F₇ H 4.5(br,2H), 7.41(s, 1H), 7.81(d,1H), 8.05(d,1H). ST-13 Cl H n-C₃F₇ H 4.1(br,2H), 6.83(d, 1H), 7.24(d,1H), 7.43(s,1H). ST-14 Br H C₂F₅ H ST-15 OCH₃ H C₂F₅ H 3.85(br,2H), 3.93(s, 3H), 6.72(d,1H), 6.92(s,1H), 7.03(d, 1H). ST-16 OCH₃ H i-C₃F₇ H ST-17 OC₂H₅ H i-C₃F₇ H ST-18 C₂H₅ H C₂F₅ H 1.29(t,3H), 2.52(q, 2H), 3.95(br,2H), 6.8(d,1H), 7.2- 7.26(m,2H). ST-19 C₂H₅ H i-C₃F₇ H ST-20 i-C₃F₇ H i-C₃F₇ H ST-21 n-C₄H₉ H C₂F₅ H 0.9(t,3H), 1.4(q, 2H), 1.6(q,2H), 2.5(t,2H), 3.95(br, 2H), 6.69(d,2H), 7.19-7.21(m,2H). ST-22 CF₃ H C₂F₅ H 4.52(br,2H), 6.81(d, 1H), 7.48(d,1H), 7.63(br,1H). ST-23 CF₃ H i-C₃F₇ H

Agricultural and horticultural insecticides containing the phthalic acid diamide derivative of the general formula (I) of the present invention as an active ingredient are suitable for controlling various insect pests such as agricultural insect pests, forest insect pests, horticultural insect pests, stored grain insect pests, sanitary insect pests, nematodes, etc., which are injurious to paddy rice, fruit trees, vegetables, other crops, flowers and ornamental plants, etc. They have a marked insecticidal effect, for example, on LEPIDOPTERA including summer fruit tortrix (Adoxophyes orana fasciata), smaller tea tortrix (Adoxophyes sp.), Manchurian fruit moth (Grapholita inopinata), oriental fruit moth (Grapholita molesta), soybean pod border (Leguminivora glycinivorella), mulberry leafroller (Olethreutes mori), tea leafroller (Caloptilia thevivora), Caloptilia sp. (Calopilia zachrysa), apple leafminer (Phyllonorycter ringoniella), pear barkniner (Spulerrina astaurota), common white (Piers rapae crucivora), tabacco budworm (Heliothis sp.), codling moth (Laspey resia pomonella), diamondback moth (Plutella xylostella), apple fruit moth (Argyresthia conjugella), peach fruit moth (Carposina niponensis), rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis), tabacco moth (Ephestia elutella), mulberry pyralid (Glyphodes pyloalis), yellow rice borer (Scirpophaga incertulas), rice skipper (Parnara guttata), rice armyworm (Pseudaletia separata), pink borer (Sesamia inferens), common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), etc.; HEMIPTERA including aster leafhopper (Macrosteles fascifrons), green rice leafhopper (Nephotettix cincticeps), brown rice planthopper (Nilaparvata lugens), whitebacked rice planthopper (Sogatella furcifera), citrus psylla (Diaphorina citri), grape whitefly (Aleurolobus taonabae), sweetpotato whitefly (Bemisia tabaci), greenhouse whitefly (Trialeurodes vaporariorum), turnip aphid (Lipaphis erysimi), green peach aphid (Myzus persicae), Indian wax scale (Ceroplastes ceriferus), cottony citrus scale (Pulvinaria aurantii), camphor scale (Pseudaonidia duplex), San Jose scale (Comstockaspis perniciosa), arrowhead scale (Unaspis vanonensis), etc.; COLEOPTERA including soybean beetle (Anomala rufocuprea), Japanese beetle (Popillia japonica), tabacco beetle (Lasioderma serricorne), powderpost beetle (Lyctus brunneus), twenty-eight-spotted ladybird (Epilachna vigintiotopunctata), adzuki bean weevile (Callosobruchus chinensis), vegetable weevil (Listroderes costirostris), maize weevil (Sitophilus zeamais), boll weevil (Anthonomus gradis gradis), rice water weevil (Lissorhoptrus orvzophilus), cucurbit leaf beetle (Aulacophora femoralis), rice leaf beetle (Oulema oryzae), striped flea beetle (Phyllotreta striolata), pine shoot beetle (Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata), Mexican bean beetle (Epilachna varivestis), corn rootworm (Diabrotica sp.), etc.; DIPTERA including melon fly (Dacus(Zeugodacus) cucurbitae), oriental fruit fly (Dacus(Bactrocera) dorsalis), rice leafminer (Agnomyza oryzae), onion maggot (Delia antiqua), seedcorn maggot (Delia platura), soybean pod gall midge (Asphondylia sp.), muscid fly (Musca domestica), house mosquito (Culex piliens pipiens), etc.; and TYLENCHIDA including root-lesion nematode (Pratylenchus sp.), coffer root-lesion nematode (Pratylenchus coffeae), potato cyst nematode (Globodera rostochiensis), root-knot nematode (Meloidogyne sp.), citrus nematode (Tylenchulus semipenetrans), Aphelenchus sp. (Aphelenchus avenae), chrysanthemum foliar (Aphelenchoides ritzemabosi), etc.

The agricultural and horticultural insecticide containing the phthalic acid diamide derivative of the general formula (I) of the present invention as an active ingredient has a marked insecticidal effect on the above-exemplified insect pests, sanitary insect pests, and/or nematodes, which are injurious to paddy field crops, upland crops, fruit trees, vegetables, other crops, flowers and ornament plants, and the like. Therefore, the desired effect of the agricultural and horticultural insecticide of the present invention can be obtained by applying the insecticide to the paddy field water, stalks and leaves of fruit trees, vegetables, other crops, flowers and ornament plants, soil, etc. at a season at which the insect pests, sanitary pests or nematodes are expected to appear, before their appearance or at the time when their appearance is confirmed.

In general, the agricultural and horticultural insecticide of the present invention is used after being prepared into conveniently usable forms according to an ordinary manner for preparation of agrochemicals.

That is, the phthalic acid diamide derivative of the general formula (I) and, optionally, an adjuvant are blended with a suitable inert carrier in a proper proportion and prepared into a suitable preparation form such as a suspension, emulsifiable concentrate, soluble concentrate, wettable powder, granules, dust or tablets through dissolution, dispersion, suspension, mixing, impregnation, adsorption or sticking.

The inert carrier used in this invention may be either solid or liquid. As the solid carrier, there can be exemplified soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residues of vegetables, powdered synthetic polymers or resins, clays (e.g. kaolin, bentonite, and acid clay), talcs (e.g. talc and pyrophyllite), silica powders or flakes (e.g. diatomaceous earth, silica sand, mica and white carbon, i.e. synthetic, high-dispersion silicic acid, also called finely divided hydrated silica or hydrated silicic acid, some of commercially available products contain calcium silicate as the major component), activated carbon, powdered sulfur, powdered pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate powder, calcium phosphate powder and other inorganic or mineral powders, chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride), and compost. These carriers may be used alone or as a mixture thereof.

The liquid carrier is that which itself has solubility or which is without such solubility but is capable of dispersing an active ingredient with the aid of an adjuvant. The following are typical examples of the liquid carrier and can be used alone or as a mixture thereof. Water; alcohols such as methanol, ethanol, isopropanol, butanol and ethylene glycol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone; ethers such as ethyl ether, dioxane, Cellosolve, dipropyl ether and tetrahydrofuran; aliphatic hydrocarbons such as kerosene and mineral oils; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalenes; halogenated hydrocarbons such as dichloroethane, chloroform, carbon tetrachloride and chlorobenzene; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate; amides such as dimethylformamide, diethylformamide and dimethylacetamide; nitriles such as acetonitrile; and dimethyl sulfoxide.

The following are typical examples of the adjuvant, which are used depending upon purposes and used alone or in combination in some cases, or need not to be used at all.

To emulsify, disperse, dissolve and/or wet an active ingredient, a surfactant is used. As the surfactant, there can be exemplified polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan mono-laurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalenesulfonic acid condensation products, ligninsulfonates and higher alcohol sulfate esters.

Further, to stabilize the dispersion of an active ingredient, tackify it and/or bind it, there may be used adjuvants such as casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl alcohols, turpentine, bran oil, bentonite and ligninsulfonates.

To improve the flowability of a solid product, there may be used adjuvants such as waxes, stearates and alkyl phosphates.

Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for dispersible products.

Adjuvants such as silicon oils may also be used as a defoaming agent.

The content of the active ingredient may be varied as required. In dusts or granules, the suitable content thereof is from 0.01 to 50% by weight. In emulsifiable concentrates or flowable wettable powders, it is also from 0.01 to 50% by weight.

The agricultural and horticultural insecticide of the present invention is used to control a variety of insect pests in the following manner. That is, it is applied to a crop on which the insect pests are expected to appear or a site where the appearance of the insect pests is undesirable, as it is or after being properly diluted with or suspended in water or the like, in an amount effective for control of the insect pests.

The applying dosage of the agricultural and horticultural insecticide of the present invention is varied depending upon various factors such as a purpose, insect pests to be controlled, a growth state of a plant, tendency of insect pests appearance, weather, environmental conditions, a preparation form, an application method, an application site and an application time. It may be properly chosen in a range of 0.1 g to 10 kg (in terms of the active ingredient) per 10 ares depending upon purposes.

The agricultural and horticultural insecticide of the present invention may be used in admixture with other agricultural and horticultural disease or pest controllers in order to expand both spectrum of controllable diseases and insect pest species and the period of time when effective applications are possible or to reduce the dosage.

Typical examples of the present invention are described below, but they should not be construed as limiting the scope of the invention.

EXAMPLES Example 1

(1-1) Production of 3-Chloro-N-[4-(1,1,2,2-tetrafluoroethoxy)-2-methylphenyl]phthalimide

In 10 ml of acetic acid were dissolved 0.55 g of 3-chlorophthalic anhydride and 0.67 g of 4-(1,1,2,2-tetrafluoroethoxy)-2-methylaniline, and the reaction was carried out with heating under reflux for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the resulting residue was washed with an ether-hexane mixed solvent to obtain 1.1 g of the desired compound.

Physical property: m.p. 121-122° C. Yield: 95%.

(1-2) Production of 3-Chloro-N¹-[4-(1,1,2,2-tetrafluoroethoxy)-2-methylphenyl]-N²-isopropylphthalic Acid Diamide (Compound No. 141) and 6-Chloro-N¹-[4-(1,1,2,2-tetrafluoroethoxy)-2-methylphenyl]-N²-isopropylphthalic Acid Diamide (Compound No. 239)

In 10 ml of dioxane was dissolved 1.1 g of 3-chloro-N-[4-(1,1,2,2-tetrafluoroethoxy)-2-methylphenyl]phthalimide, followed by adding thereto 0.5 g of isopropylamine, and the reaction was carried out at 80° C. for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography using a hexane/ethyl acetate (2/1) mixed solvent as an eluent, to obtain 0.4 g of the desired compound (compound No. 141) having an Rf value of 0.5 to 0.7 and 0.5 g of the other desired compound (compound No. 239) having an Rf value of 0.2 to 0.4.

Compound No. 141:

Physical property: m.p. 202-204° C. Yield: 31%.

Compound No. 239:

Physical property: m.p. 199-201° C. Yield: 39%.

Example 2

(2-1) Production of N-(4-Trifluoromethoxyphenyl)-3-nitrophthalimide

In 50 ml of acetic acid were dissolved 5.97 g of 3-nitrophthalic anhydride and 5.31 g of 4-trifluoromethoxyaniline, and the reaction was carried out with heating under reflux for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the resulting residue was washed with an ether-hexane mixed solvent to obtain 10.2 g of the desired compound.

Physical property: m.p. 149-150° C. Yield: 97%.

(2-2) Production of 3-Amino-N-(4-trifluoromethoxyphenyl)phthalimide

In a pressure vessel were placed 10.0 g of N-(4-trifluoromethoxyphenyl)-3-nitrophthalimide, 100 ml of acetic acid and 0.5 g of 5% palladium carbon, and catalytic reduction with hydrogen was carried out at a hydrogen pressure of 5 kg/cm². After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. The resulting residue was washed with an ether-hexane mixed solvent to obtain 9.0 g of the desired compound.

Physical property: m.p. 161-162° C. Yield: 98%.

(2-3) Production of 3-Bromo-N-(4-trifluoromethoxyphenyl)phthalimide

In 20 ml of acetic acid was dissolved 1.6 g of 3-amino-N-(4-trifluoromethoxyphenyl)phthalimide, and a solution of 0.35 g of sodium nitrite in 5 ml of concentrated sulfuric acid was added dropwise while maintaining the temperature at 15° C. or lower. The resulting mixture was stirred at 15° C. or lower for another 20 minutes to obtain a diazonium salt. The diazonium salt was slowly added to a mixture of a solution of 0.86 g of cuprous bromide in 50 ml of hydrobromic acid and 10 ml of toluene which was maintained at 80° C. The resulting mixture was stirred until foaming ceased. After completion of the reaction, the organic layer was washed with an aqueous sodium thiosulfate solution and an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel chromatography to obtain 1.3 g of the desired compound.

Physical property: m.p. 117-118° C. Yield: 67%.

(2-4) Production of 3-Bromo-N¹-(4-trifluoromethoxyphenyl)-N²-isopropylphthalic Acid Diamide (Compound No. 262) and 6-Bromo-N¹-(4-trifluoromethoxyphenyl)-N²-isopropylphthalic Acid Diamide (Compound No. 302)

From 1.3 g of 3-bromo-N-(4-trifluoromethoxyphenyl)phthalimide, 0.5 g of the desired compound (compound No. 262) and 0.7 g of the other desired compound (compound No. 302) were obtained in the same manner as in Example 1-2.

Compound No. 262:

Physical property: m.p. 208-210° C. Yield: 33%.

Compound No. 302:

Physical property: m.p. 210-212° C. Yield: 47%.

Example 3

(3-1) Production of N-(4-Difluoromethoxy-2-methylphenyl)-3-nitrophthalimide

In 100 ml of acetic acid were dissolved 5.8 g of 3-nitrophthalic anhydride and 5.2 g of 4-difluoromethoxy-2-methylaniline, and the reaction was carried out with heating under reflux for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the resulting residue was washed with an ether-hexane mixed solvent to obtain 10.2 g of the desired compound.

Physical property: m.p. 163-164° C. Yield: 98%.

(3-2) Production of N¹-(4-Difluoromethoxy-2-methylphenyl)-N²-isopropyl-3-nitrophthalic Acid Diamide (Compound No. 696)

In 100 ml of dioxane was dissolved 10 g of N-(4-difluoromethoxy-2-methylphenyl)-3-nitrophthalimide, followed by adding thereto 2.5 g of isopropylamine, and the reaction was carried out for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the resulting residue was washed with ether to obtain 4.0 g of the desired compound.

Physical property: m.p. 148-149° C. Yield: 86%.

(3-3) Production of 3-Amino-N¹-(4-difluoromethoxy-2-methylphenyl)-N²-isopropylphthalic Acid Diamide

In a pressure vessel were placed 5 g of N¹-(4-difluoromethoxy-2-methylphenyl)-N²-isopropyl-3-nitrophthalic acid diamide, 50 ml of acetic acid and 0.25 g of 5% palladium carbon, and catalytic reduction with hydrogen was carried out at a hydrogen pressure of 5 kg/cm². After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. The resulting residue was washed with an ether-hexane mixed solvent to obtain 4.0 g of the desired compound.

Physical property: m.p. 148-149° C. Yield: 86%.

(3-4) Production of N¹-(4-Difluoromethoxy-2-methylphenyl)-3-iodo-N²-isopropylphthalic Acid Diamide (Compound No. 387)

In 20 ml of acetic acid was dissolved 1.89 g of 3-amino-N¹-(4-difluoromethoxy-2-methylphenyl)-N²-isopropylphthalic acid diamide, and 1.5 g of concentrated sulfuric acid was added under ice-cooling. While maintaining the resulting solution at 15° C. or lower, a solution of 0.35 g of sodium nitrite in 0.5 ml of water was added dropwise. The resulting solution was stirred at 15° C. or lower for another 20 minutes to obtain a diazonium salt. The diazonium salt was slowly added to a mixture of 50 ml of an aqueous solution containing 1.0 g of potassium iodide and 50 ml of chloroform which was maintained at 40° C. The resulting mixture was stirred until foaming ceased. After completion of the reaction, the organic layer was washed with an aqueous sodium thiosulfate solution and an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel chromatography to obtain 0.8 g of the desired compound.

Physical property: m.p. 207-209° C. Yield: 33%.

Example 4

(4-1) Production of 3-Iodo-2-N-isopropyl-phthalamic Acid

A solution of 0.67 g of isopropylamine in 5 ml of acetonitrile was added dropwise to a solution of 1.37 g of 3-iodophthalic anhydride in 10 ml of acetonitrile under ice-cooling, and the reaction was carried out with stirring at room temperature for another 5 hours. After completion of the reaction, the crystals formed in the reaction solution were collected by filtration and washed with a small volume of acetonitrile to obtain 1.45 g of the desired compound.

Yield: 87%. ¹H-NMR [CDCl₃/TMS, δ values (ppm)]; 1.23 (6H, d), 4.35 (1H, m), 5.80 (1H, d), 6.85 (1H, broad), 7.07 (1H, t), 7.93 (1H, d), 7.96 (1H, d).

(4-2) Production of 6-Iodo-N-isopropyl-phthalic Acid Isoimide

In 10 ml of toluene was dissolved 0.45 g of 3-iodo-2-N-isopropyl-phthalamic acid, followed by adding thereto 0.85 g of trifluoroacetic anhydride, and the reaction was carried out with stirring for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 0.43 g of the desired compound as a crude product. The obtained desired compound was used in the subsequent reaction without purification.

Physical property: m.p. 87.5-88.5° C.

(4-3) Production of 3-Iodo-N¹-(4-pentafluoroethyl-2-methylphenyl)-N2-isopropyl-phthalic Acid Diamide (Compound No. 372)

In 10 ml of tetrahydrofuran was dissolved 0.43 g of the 6-iodo-N-isopropyl-phthalic acid isoimide obtained in 4-2, followed by adding thereto 0.30 g of 4-pentafluoroethyl-2-methylaniline, and the reaction was carried out with stirring for 1 hour. After completion of the reaction, the solvent was removed from the reaction solution by distillation under reduced pressure, and the resulting residue was washed with ether-n-hexane to obtain 0.70 g of the desired compound.

Physical property: m.p. 195-196° C. Yield: 95%.

Example 5

(5-1) Production of Ethyl 6-Nitro-N-(4-chloro-2-methylphenyl)-phthalamate

In 30 ml of tetrahydrofuran was dissolved 1.29 g of 3-nitro-2-ethoxycarbonylbenzoyl chloride, followed by adding thereto 0.71 g of 4-chloro-2-methylaniline and 0.56 g of triethylamine, and the reaction was carried out with stirring for 30 minutes. After completion of the reaction, the reaction solution containing the desired compound was poured into water and the desired compound was extracted with ethyl acetate. The extracted solution was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography to obtain 1.7 g of the desired compound.

Physical property: m.p. 164-165° C. Yield: 94%.

(5-2) Production of 3-Nitro-N¹-(4-chloro-2-methylphenyl)-N²-isopropyl-phthalic Acid Diamide (Compound No. 664)

In 20 ml of dioxane was dissolved 1.7 g of ethyl 6-nitro-N-(4-chloro-2-methylphenyl)-phthalamate, followed by adding thereto 1.5 g of isopropylamine, and the reaction was carried out with stirring at 80° C. for 1 hour. After completion of the reaction, the solvent was removed from the reaction solution containing the desired compound, by distillation under reduced pressure, and the resulting residue was purified by a silica gel column chromatography to obtain 1.5 g of the desired compound.

Physical property: m.p. 202-204° C. Yield: 85%.

Example 6

(6-1) Production of N-Isopropyl-3,4-dichlorophthalamic Acid

In 30 ml of tetrahydrofuran was dissolved 2.32 g of N-isopropyl-3,4-dichlorobenzamide, and 21 ml of s-BuLi (0.96 M/L) was slowly added while maintaining the temperature at −70° C. The resulting mixture was stirred at −70° C. for 30 minutes, after which the cooling bath was removed. An excess of carbon dioxide was introduced into the reaction solution, and the thus treated solution was stirred at room temperature for 30 minutes to carry out the reaction.

After completion of the reaction, the reaction solution was poured into water and acidified with diluted hydrochloric acid, and the desired compound was extracted with ethyl acetate. The extracted solution was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, and the crystals thus obtained were washed with an ether-hexane mixed solvent to obtain 2.4 g of the desired compound.

Physical property: m.p. 155-156° C. Yield: 86.9%.

(6-2) Production of N-Isopropyl-3,4-dichlorophthalic Acid Isoimide

In 10 ml of toluene was dissolved 0.41 g of N-isopropyl-3,4-dichlorophthalamic acid, followed by adding thereto 0.42 g of trifluoroacetic anhydride, and the reaction was carried out with stirring at room temperature for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 0.39 g of the desired compound as a crude product. The obtained desired compound was used in the subsequent reaction without purification.

(6-3) Production of 3,4-Dichloro-N¹-(4-pentafluoroethyl-2-methylphenyl)-N²-isopropylphthalic Acid Diamide (Compound No. 1222)

In 10 ml of acetonitrile was dissolved 0.39 g of N-isopropyl-3,4-dichlorophthalic acid isoimide, followed by adding thereto 0.34 g of 4-pentafluoroethyl-2-methylaniline, and the reaction was carried out with stirring for 2 hours. After completion of the reaction, the reaction solution was maintained at 0° C. for 10 minutes and the crystals precipitated were collected by filtration and washed with hexane to obtain 0.61 g of the desired compound.

Physical property: m.p. 208-209° C. Yield: 84.1%.

Example 7

Production of 3-Chloro-2-isopropylaminothiocarbonyl-N-(pentafluoroethyl-2-methylphenyl)benzamide (Compound No. S-1)

In 20 ml of tetrahydrofuran was dissolved 1.06 g of N-(pentafluoroethyl-2-methylphenyl)-3-chlorobenzamide, and 7 ml of s-BuLi (0.96 M/L) was slowly added while maintaining the temperature at −70° C. The resulting mixture was stirred at −70° C. for 30 minutes, after which the cooling bath was removed. A solution of 0.33 g of isopropyl isothiocyanate in 5 ml of tetrahydrofuran was poured into the reaction solution, and the resulting solution was stirred at room temperature for 30 minutes to carry out the reaction.

After completion of the reaction, the reaction solution was poured into water and acidified with diluted hydrochloric acid, and the desired compound was extracted with ethyl acetate. The extracted solution was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, and the crystals thus obtained were washed with an ether-hexane mixed solvent to obtain 1.2 g of the desired compound.

Physical property: m.p. 162-164° C. Yield: 86%.

Example 8

Production of 2-Methyl-4-pentafluoroethylaniline (Compound No. ST-3)

In an autoclave were placed 11.7 g (0.05 mole) of 2-methyl-4-iodoaniline, 6.4 g of copper powder, 18.5 g of iodopentafluoroethane and 100 ml of DMSO, and the reaction was carried out with stirring for 6 hours while maintaining the internal temperature at 120° C. After completion of the reaction, the reaction mixture was cooled to room temperature, poured into 500 ml of ice water, and thoroughly stirred. Then, the insoluble materials were removed and the desired compound was extracted with 300 ml of ethyl acetate. The extract solution was washed with water, dried over anhydrous sodium sulfate and then concentrated, after which the residue was purified by vacuum distillation to obtain 9.8 g of the desired compound.

Physical property: b.p. 95-105° C./10 mmHg. Yield: 87%.

Example 9

(9-1). Production of 2-Ethyl-4-pentafluoroethylacetanilide

In an autoclave were placed 4.0 g (0.0138 mole) of 2-ethyl-4-iodoacetanilide, 1.8 g of copper powder, 5.1 g of iodopentafluoroethane and 40 ml of DMSO, and the reaction was carried out with stirring for 6 hours while maintaining the internal temperature at 120° C. After completion of the reaction, the reaction mixture was cooled to room temperature, poured into 200 ml of ice water, and thoroughly stirred. Then, the insoluble materials were removed and the desired compound was extracted with 200 ml of ethyl acetate. The extract solution was washed with water, dried over anhydrous sodium sulfate and then concentrated, after which the residue was purified by a silica gel column chromatography to obtain 0.7 g (yield: 18%) of the desired compound.

(9-2). Production of 2-Ethyl-4-pentafluoroethylaniline (Compound No. ST-18)

To 10 ml of a 6N aqueous hydrochloric acid solution was added 0.6 g (2.1 mmoles) of 2-ethyl-4-pentafluoroethylacetanilide, and the reaction was carried out with heating under reflux for 2 hours. After completion of the reaction, the reaction solution was ice-cooled and then neutralized with a 10% aqueous sodium hydroxide solution, and the desired compound was extracted with ethyl acetate. The extract solution was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 0.4 g of the desired compound.

Physical Property:

¹H-NMR (δ, ppm); 1.29 (t, 3H), 2.52 (q, 2H), 3.95 (br, 2H), 6.8 (d, 1H), 7.2-7.26 (m, 2H). Yield: 80%.

Example 10

Production of 2-Chloro-4-pentafluoroethylaniline (Compound No. ST-11)

In an autoclave were placed 5.0 g (19.7 mmoles) of 2-chloro-4-iodoaniline, 2.8 g of copper powder, 10.0 g of iodopentafluoroethane and 50 ml of DMF, and the reaction was carried out with stirring for 20 hours while maintaining the internal temperature at 135° C. After completion of the reaction, the reaction mixture was cooled to room temperature, poured into 200 ml of ice water, and thoroughly stirred. Then, the insoluble materials were removed and the desired compound was extracted with 200 ml of ethyl acetate. The extract solution was washed with water, dried over anhydrous sodium sulfate and then concentrated, after which the residue was purified by a silica gel column chromatography to obtain 4.2 g of the desired compound.

Physical Property:

¹H-NMR (δ, ppm) 4.4 (br, 2H), 6.8 (d, 1H), 7.27 (dd, 1H), 7.47 (d, 1H). Yield: 87%.

Example 11

Production of 2-Trifluoromethyl-4-pentafluoroethylaniline (Compound No. ST-22)

In an autoclave were placed 6.0 g (20.9 moles) of 2-trifluoro-4-iodoaniline, 2.8 g of copper powder, 11.1 g of iodopentafluoroethane and 40 ml of DMF, and the reaction was carried out with stirring for 7 hours while maintaining the internal temperature at 135° C. After completion of the reaction, the reaction mixture was cooled to room temperature, poured into 200 ml of ice water, and thoroughly stirred. Then, the insoluble materials were removed and the desired compound was extracted with 200 ml of ethyl acetate. The extract solution was washed with water, dried over anhydrous sodium sulfate and then concentrated, after which the residue was purified by a silica gel column chromatography to obtain 3.9 g of the desired compound.

Physical Property:

¹H-NMR (δ, ppm) 4.52 (br, 2H), 6.81 (d, 1H), 7.27 (dd, 1H), 7.48 (d, 1H), 7.63 (br, 1H). Yield: 67%.

Example 12

(12-1). Production of 2-Methyl-4-(heptafluoropropan-2-yl)-nitrobenzene

In an autoclave were placed 12.0 g (0.0456 mole) of 4-iodo-2-methylnitrobenzene, 11.6 g of copper powder, 40 g of 2-iodoheptafluoropropane and 200 ml of DMF, and the reaction was carried out with stirring for 6 hours while maintaining the internal temperature at 140° C. After completion of the reaction, the reaction mixture was cooled to room temperature, poured into 600 ml of ice water, and thoroughly stirred. Then, the insoluble materials were removed and the desired compound was extracted with 300 ml of hexane. The extract solution was washed with water, dried over anhydrous sodium sulfate and then concentrated, after which the residue was purified by vacuum distillation to obtain 11.4 g of the desired compound.

Physical property: b.p. 120-125° C./10 mmHg. Yield: 82%.

(12-2). Production of 2-Methyl-4-(heptafluoropropan-2-yl)-aniline (Compound No. ST-4)

In 60 ml of ethanol was dissolved 11.4 g (0.0374 mole) of 2-methyl-4-(heptafluoropropan-2-yl)-nitrobenzene, and a solution of 29.5 g of SnCl₂.2H₂O in 40 ml of hydrochloric acid was added dropwise thereto under ice-cooling over a period of 30 minutes. After completion of the dropwise addition, the reaction was carried out at room temperature for 2 hours. After completion of the reaction, the reaction solution was poured into 200 ml of ice water and neutralized with a 40% aqueous sodium hydroxide solution under ice-cooling. Then, a 40% aqueous sodium hydroxide solution was further added thereto until a homogeneous solution was obtained, and the desired compound was extracted with 100 ml of ether. The extract solution was washed with water, dried over anhydrous sodium sulfate and then concentrated, after which the residue was purified by vacuum distillation to obtain 9.8 g of the desired compound.

Physical property: b.p. 100-110° C./10 mmHg. Yield: 95%.

Example 13

Production of 3-Bromo-N¹-(4-nonafluorobutyl-2-methylphenyl)-N 2-isopropyl-phthalic Acid Diamide (Compound No. 281)

In 10 ml of tetrahydrofuran was dissolved 0.54 g of 6-bromo-N-isopropyl-phthalic acid isoimide, followed by adding thereto 0.30 g of 2-methyl-4-nonafluorobutylaniline, and the reaction was carried out with stirring for 1 hour. After completion of the reaction, the solvent was removed from the reaction solution by distillation under reduced pressure, and the resulting residue was washed with ether-n-hexane to obtain 1.1 g of the desired compound.

Physical property: m.p. 190-191° C. Yield 94%.

Typical preparation examples and test examples of the present invention are described below but they should not be construed as limiting the scope of the invention.

In the preparation examples, parts are all by weight.

Formulation Example 1

Each compound listed in Table 1 50 parts Xylene 40 parts Mixture of polyoxyethylene 10 parts nonylphenyl ether and calcium alkylbenzenesulfonate

An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect dissolution.

Formulation Example 2

Each compound listed in Table 1  3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts

A dust was prepared by mixing uniformly and grinding the above ingredients.

Formulation Example 3

Each compound listed in Table 1  5 parts Mixed powder of bentonite and clay 90 parts Calcium lignin sulfonate  5 parts

Granules were prepared by mixing the above ingredients uniformly, and kneading the resulting mixture together with a suitable amount of water, followed by granulation and drying.

Formulation Example 4

Each compound listed in Table 1 20 parts Mixture of kaolin and synthetic 75 parts high-dispersion silicic acid Mixture of polyoxyethylene  5 parts nonylphenyl ether and calcium alkylbenzenesulfonate

A wettable powder was prepared by mixing uniformly and grinding the above ingredients.

Test Example 1

Insecticidal Effect on Diamondback Moth (Plutella xylostella)

Adult diamondback moths were released and allowed to oviposit on a Chinese cabbage seedling. Two days after the release, the seedling having eggs deposited thereon was immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Table 1 as an active ingredient to adjust the concentration to 500 ppm. After air-drying, it was allowed to stand in a room thermostated at 25° C. Six days after the immersion, the hatched insects were counted. The mortality was calculated according to the following equation and the insecticidal effect was judged according to the criterion shown below. The test was carried out with triplicate groups of 10 insects. $\begin{matrix} {Corrected} \\ {{mortality}\quad (\%)} \end{matrix} = {\frac{\begin{bmatrix} {{Number}\quad {of}} \\ {{hatched}\quad {insects}} \\ {{in}\quad {untreated}\quad {group}} \end{bmatrix} - \begin{bmatrix} {{Number}\quad {of}} \\ {{hatched}\quad {insects}} \\ {{in}\quad {treated}\quad {group}} \end{bmatrix}}{\begin{bmatrix} {{Number}\quad {of}} \\ {{hatched}\quad {insects}} \\ {{in}\quad {untreated}\quad {group}} \end{bmatrix}} \times 100}$

Criterion: Effect Mortality (%) A 100 B 99-90 C 89-80 D 79-50

The results obtained are shown in Table 5.

Test Example 2 Insecticidal Effect on Common Cutworm (Spodoptera Litura)

A piece of cabbage leaf (cultivar; Shikidori) was immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Table 1 as an active ingredient to adjust the concentration to 500 ppm. After air-drying, it was placed in a plastic Petri dish with a diameter of 9 cm and inoculated with second-instar larvae of common cutworm, after which the dish was closed and then allowed to stand in a room thermostated at 25° C. Eight days after the inoculation, the dead and alive were counted. The mortality was calculated according to the following equation and the insecticidal effect was judged according to the criterion shown in Test Example 1. The test was carried out with triplicate groups of 10 insects. $\begin{matrix} {Corrected} \\ {{mortality}\quad (\%)} \end{matrix} = {\frac{\begin{bmatrix} {{Number}\quad {of}} \\ {{alive}\quad {larvae}\quad {in}} \\ {{untreated}\quad {group}} \end{bmatrix} - \begin{bmatrix} {{Number}\quad {of}} \\ {{alive}\quad {larvae}\quad {in}} \\ {{treated}\quad {group}} \end{bmatrix}}{\begin{bmatrix} {{Number}\quad {of}} \\ {{alive}\quad {larvae}\quad {in}} \\ {{untreated}\quad {group}} \end{bmatrix}} \times 100}$

The results obtained are shown in Table 5.

Test Example 3

Insecticidal Effect on Rice Leafroller (Cnaphalocrocis medinalis)

The lamina of a rice plant at the 6 to 8 leaf stage was immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Table 1 as an active ingredient to adjust the concentration to 500 ppm. After air-drying, the lamina was placed in a plastic Petri dish with a diameter of 9 cm whose bottom had been covered with a wetted filter paper. The lamina was inoculated with third-instar larvae of rice leafroller, after which the dish was allowed to stand in a room thermostated at 25° C. and having a humidity of 70%. Four days after the inoculation, the dead and alive were counted and the insecticidal effect was judged according to the criterion shown in Test Example 1. The test was carried out with triplicate groups of 10 insects.

The results obtained are shown in Table 5.

TABLE 5 Test Example Test Example Test Example No 1 2 3 1 D D A 2 A C 3 C A 4 A D 7 A 8 A A A 9 A A 10 A D D 11 A C C 12 A D 13 D D 14 A 15 A A 16 A 17 A D 18 D A 20 A 22 A D 23 A D 24 A D 25 A A 26 A D 27 A A C 28 A 29 A B A 30 A A A 31 A 32 A 33 A 34 A C 37 A 41 A A 42 A D A 43 B D 44 A 45 A A 46 A B 47 A D A 48 A B A 49 A A A 50 A A A 51 A A 52 A A A 53 A A 55 A B A 56 A A A 58 A A A 59 A 60 A A A 61 A B A 62 A A A 63 A B A 64 A B A 65 A A A 66 A A B 67 A A A 68 A 69 A A 70 A A 71 D 73 A 74 A 75 A A 76 C B 77 A C A 78 A A A 79 A A D 81 A 83 A A A 84 A 86 B B 87 A A 88 A 89 A B A 90 A A B 91 A A A 92 A 93 A A A 98 A C 99 A A 100 A A A 101 A 102 A D A 103 A C A 109 A A C 110 A A 111 A C B 112 A A A 113 A B A 114 A A A 115 A C A 116 A D A 117 A A A 118 A A A 119 A A A 120 A D A 121 A A A 122 A A A 123 A A 124 A A A 125 A B A 126 A A A 127 A A A 128 A D A 129 A A A 130 A A A 132 A A A 133 A A A 134 A A 135 A A A 136 A A A 137 A A 138 A A A 139 A A A 140 A A A 141 A A A 142 A A B 143 A A A 144 A A A 145 A A A 146 A A A 147 A C 148 A A A 149 A A A 150 A A A 151 A 152 A A A 153 A D 157 A A A 158 A A A 159 A A A 161 A D A 162 A A B 163 A A A 164 A A 165 A B C 167 A A A 168 A 169 A D 170 A D B 171 A D 172 A A D 173 A D D 174 A 175 A 176 A D A 177 A A A 178 A A 179 A 180 A A A 181 A 183 A B 185 A 186 D 187 A D 188 D D 189 A 190 A 191 A A 192 A 193 A D 194 A 195 A 196 A D 197 A A A 198 A C A 199 A 200 A A 201 A B A 202 A 203 A 206 A A 207 A 208 A 209 A B 210 A D 211 A A 212 A D A 213 A A A 214 A A A 215 A D 216 A A 217 A A 218 A C 219 A D A 220 A A 221 A A A 222 A B A 223 A A A 225 A B A 226 A A 227 A 228 B A 229 A D A 230 A C A 231 B A 232 A A 233 A 234 A A 235 A A 236 A A A 237 A A 238 A A 239 A A A 240 A 241 A B A 242 A B A 243 A A B 244 A C 245 A D 246 A B B 248 A C 249 A D A 250 A D 251 A A 252 A 253 A A C 254 A A 255 A A 256 A 257 A B 258 A A 259 A D 261 A A D 262 A A D 263 A A 264 — D A 265 A 266 A A A 267 A A A 268 A A A 269 A A A 270 A A A 271 A A A 272 A A A 273 A D D 274 A A A 275 A D A 276 A A A 277 A A A 278 A A A 279 A A A 281 A A A 282 A A A 283 A A A 284 A A A 285 A D A 286 A A A 287 A A A 288 A A A 289 A A A 290 A A A 291 A A A 292 A A A 293 A A A 294 A A A 295 D 296 A A A 297 A A B 298 A A A 299 A A A 300 A A 301 A A D 302 A D 303 A D 304 A 305 A A A 306 A A A 307 A D 308 A 309 A A 310 A 311 A D 312 A A A 313 A A A 314 A A 315 A A 316 A A A 318 A B A 319 A B B 320 A D 321 A A 322 A B 323 A C A 324 A A 325 A A A 326 A A 327 A A 328 A A A 329 A A A 330 A A 332 A A 333 A D 334 A C C 335 A B 336 A D 337 A A 338 A B A 339 A B A 340 A A 341 A A 342 A 343 A 345 A B A 346 A C A 347 A B C 348 A A 349 A 350 A A A 351 A A A 352 A 353 A A A 354 A A A 355 A C A 356 A A A 360 A D A 361 A A A 362 A A A 363 A A A 364 A A D 365 A A A 366 A A A 367 A A A 368 A A A 369 A A A 370 A A A 371 A A A 372 A A A 373 A A A 374 A A A 375 A A A 376 A A 377 A A 378 A D A 379 A A A 380 A A A 381 A A A 382 A B A 383 A A 384 A C 385 A B A 386 A A A 387 A A A 388 A A B 389 A A A 390 A A A 391 A A A 392 A A A 393 A A A 394 A A A 395 A A A 396 A A A 397 A A A 398 A 399 A A A 400 A D A 402 A 403 A B A 404 A A A 406 A A A 407 A A A 408 A B A 409 A A A 410 A A A 411 A A 412 A C 413 A C 414 A A 415 A 416 A A A 417 A A A 418 A 419 A A A 420 A D 421 A B A 422 A 424 A A 427 A D 428 A 429 A D 430 A D D 431 A A 432 A A 433 A A 434 A 435 A B A 436 A B A 437 A C A 438 A B A 439 A A A 440 A C B 441 A B 442 A 443 A D 444 A A 445 B A 446 A A A 447 A B C 448 A A 449 A 450 A C 451 A A 452 A A A 453 A D A 454 A A A 455 A B A 456 A A 457 A A B 458 A 459 A 460 A B 461 A 462 A 463 A 464 A A 465 A 466 A A 467 A A 468 A A B 469 A A D 470 A C C 471 A A A 472 A B 473 A A A 474 A B A 475 A D 476 A A A 477 A C 478 A 479 A A 480 A B A 488 A A A 489 A A A 490 A A A 491 A A A 492 A A A 493 A A A 494 A A 495 A A A 496 A A A 498 A A A 499 A A A 500 A B A 501 A A A 502 A A A 503 A B A 504 A A A 505 A A A 506 A 507 A B A 508 A B A 509 A A A 510 A B A 511 A A A 512 A A A 513 A A A 514 A A A 515 A C 516 A A A 517 A A A 518 A B 519 A A A 520 A 521 A A A 522 A D A 523 A A A 524 A A A 526 A A 527 A A A 528 A A 529 A D A 530 A D 531 A A 532 A A 533 A A A 534 A A 535 A A 536 A 537 A 538 A A A 539 A 540 A 543 A A 544 A A 545 A A 546 A A 547 A A D 548 A A A 549 A A D 550 A C A 551 A A 552 A B 553 A C A 554 A A 555 A B 557 A C B 558 A A A 559 A 560 A 561 A C A 562 A A 563 A A 564 A B 565 A A 566 A B 567 A D D 568 A C A 569 A A A 570 A A 571 A C 573 A 575 A A 576 A C 577 A A 579 A A A 580 A A 581 A B A 582 A A 584 A D 585 A A 586 A D 587 A 588 A 589 A A 590 A 591 A D 592 A 593 A 594 A 595 A A A 596 D D 597 B 598 A 599 A D A 600 A 601 A 602 A A 603 B C 604 A D 605 C 606 A D A 607 A A A 608 A 609 A B A 610 A A C 611 A A 612 A D 613 A 614 A 615 A 616 A D 617 A A A 618 A A A 619 A A A 621 A 622 A 623 A A 624 A 625 A D D 626 A 628 A B A 633 A D 634 A D 635 A D 636 A D A 637 A 638 B 639 A 640 A 641 D D 642 A 643 A A 644 A A 645 A 646 A D 647 A B 648 A D A 649 A C 650 A 652 A 653 A 654 D 656 A A 657 D 658 A 659 A 660 A A 661 B D 662 A 663 A A D 664 A A 665 A A B 666 A D 667 A A A 668 A 669 A D A 670 A D 671 A D 672 A 673 A D D 674 A D A 675 A A A 676 A C A 677 A 678 A 679 A A 680 A D 681 A A A 682 A A 683 A A A 684 A A A 686 A A A 687 A D D 688 A A 689 A D A 690 A A 691 A D C 692 A D 693 A A 694 A A 695 A A A 696 A A A 697 A A 698 A B A 699 A A D 700 A A A 701 A A A 703 A A A 704 A A 705 A D A 706 A A 708 D 709 A A 710 A C A 711 A C A 712 A A A 713 A B D 714 A A A 715 A A A 716 A A A 717 A A 718 A A 719 A D 720 A 721 A 722 A A 723 D D 724 A B 725 A A 727 A B A 728 A A 729 A A 732 A 733 A 735 D 737 A 738 D 740 A A 741 A A A 742 A 743 D 744 C 745 D 749 A 750 A A 751 A A 752 A 753 A A D 755 A A 758 A 759 D 765 A 766 A 767 A C A 768 A B A 769 A D 770 A A A 771 A C 772 A A 773 A A 774 A A 776 B D 777 A D 778 A A 780 A A A 781 A A A 782 A A 783 A A A 785 A 788 C C 790 A 791 A A 793 A 795 A B A 796 A 797 A C 798 A 799 A A 800 C 801 A A D 802 D 803 A A 808 A 819 A B A 821 A A 822 D D 824 A 825 A 826 A A 827 A 830 C 831 D D 832 A 833 A D 835 A 836 A A 837 A 838 A C A 839 A C 840 A D 841 A D 842 A A D 845 A 846 A 847 D 848 A 849 A B A 850 A A 851 A D A 852 A D 854 A 855 A 856 A D 858 C A 859 D 860 A 861 A 862 A D D 863 A B 864 A 865 A 866 D 867 A C 869 A D 870 A 871 A 872 A C 874 A C A 875 A 878 C 879 A A 880 D 881 A D 888 D 889 A A 890 A A A 891 A A A 892 A A 893 A A A 894 A A A 895 A A A 901 A D A 902 A 903 A A A 904 A 905 A A A 906 A D A 907 A A A 908 A D A 909 A A A 910 A 911 A D 912 A 913 A 914 A 915 A A A 916 A 917 A A A 918 A 919 A 920 A 924 A 925 A A 927 A A A 928 A A 929 A A A 930 A A A 931 A A A 932 A A A 933 A A 934 A A A 935 A A A 936 A A A 937 A A A 938 A A 939 A A A 940 A A A 941 A A A 942 A A A 943 A C A 944 A A A 945 A A A 946 A A 947 A A A 949 A A A 950 C 951 A A A 952 A A 953 A A A 954 A A 955 A A A 956 A A 957 A A A 958 A A 959 A A 965 A C 966 A B 971 A A A 972 A 973 A A A 974 A A A 975 A A 976 A A A 977 A A A 978 A C A 979 A A A 980 A A A 981 A A A 982 A C 983 A A A 984 A 985 A A A 986 A A 987 A A A 988 A 989 A A A 990 A A 991 A A A 992 A 993 A A 995 A A 996 A A A 997 A A A 998 A A A 999 A A 1000 A D A 1001 A A A 1002 A A A 1003 A A A 1004 A A A 1005 A A A 1006 A 1007 A A A 1008 A A 1009 A A A 1010 A A 1011 A A A 1013 A A A 1014 A A 1015 A D A 1016 A 1017 A A A 1018 A D A 1019 A A A 1020 A A A 1021 A A 1022 A A A 1023 A A A 1024 A A A 1025 A 1026 A A 1027 A 1028 A A A 1031 A A A 1032 A A 1033 A A A 1034 A 1035 A A A 1036 A A 1037 A A A 1038 A A A 1039 A A A 1040 A A A 1041 A A A 1042 A A A 1043 A A 1044 A A A 1045 A A A 1046 A A A 1047 A A 1048 A A 1049 A A A 1050 A A A 1051 A A A 1052 A A 1053 A A A 1054 A A A 1055 A A A 1056 A A A 1057 A A 1058 A A A 1059 A 1060 A A A 1061 A A A 1062 A A A 1063 A 1064 A A 1065 A 1066 A C A 1067 A A A 1068 A A A 1069 A A A 1070 A A A 1071 A C A 1072 A 1073 A A A 1074 A A A 1075 A A A 1076 A A 1077 A A 1078 A A A 1079 A A A 1080 A A A 1081 A A A 1082 A 1083 A 1086 A A 1087 A A A 1088 A A 1089 A A 1099 A A 1100 A C A 1101 A C A 1102 A A A 1103 A A 1104 A A A 1105 A A A 1106 A A 1107 A A 1108 A A 1109 A A 1110 A C A 1111 A A 1112 A A A 1113 A A A 1114 A A A 1115 A A A 1116 A A A 1117 A A A 1118 A A A 1119 A A A 1120 A A A 1121 A A A 1122 A A A 1123 A A A 1124 A A A 1125 A A A 1126 A A A 1127 A A A 1128 A A A 1129 A A A 1130 A A A 1131 A A A 1132 A A 1133 A A 1134 A A 1135 A A 1136 A A 1137 A 1138 A 1139 A 1140 A 1141 A A A 1142 A A A 1143 A C A 1144 A A A 1145 A A 1146 A C A 1147 A A A 1148 A A A 1149 A A 1150 A A A 1151 A A A 1152 A A A 1153 A A A 1154 A C A 1155 A A 1156 A A A 1157 A A 1158 A D A 1159 A A A 1160 A A A 1161 A D A 1162 A A A 1163 A A A 1164 A A A 1165 A A A 1166 A A A 1167 A A A 1168 A A A 1169 A A A 1173 A A A 1174 A A A 1175 A 1178 A 1179 A A — 1180 A — 1181 A — 1182 A — 1183 A A — 1184 A A — 1185 A C — 1186 A A — 1187 A A — 1188 A A — 1189 A A — 1190 A A A 1191 A A A 1192 A A A 1193 A A A 1202 A A A 1203 A D A 1204 A A A 1205 A A 1206 A A A 1207 A A A 1208 A A 1209 A D A 1210 A A A 1211 A A A 1212 A A A 1221 A A A 1222 A A A 1223 A A A 1224 B 1225 A 1226 A 1227 A A A 1228 A A A 1229 A A A 1230 A A A 1231 A A A 1232 A A A 1233 A A — 1234 A A — 1235 A D — 1236 A A — 1237 A A — 1238 A — 1245 A A — 1246 A A A 1247 C 1248 A A A 1249 A 1250 A A A 1251 A A A 1256 A A — 1257 A A — 1258 A A — 1259 A — 1260 A — 1261 A A — 1262 A A A 1263 A A A 1264 A A A 1266 A A 1277 A A A 1278 A A A 1280 A A A 1281 A A 1283 A — — 1284 A — A 1285 A — A 1287 A A A 1288 A 1291 A 1293 A 1294 A A A 1295 A A A 1296 A A A 1297 A A A 1298 A A A 1299 A A A 1300 A A A 1301 A A 1303 A A A 1304 A A 1305 A A A 1306 A 1307 A A A 1308 C 1309 A A A 1310 B 1311 A A A 1312 A A 1313 A A A 1314 A A A 1315 A A A 1316 A A A 1317 A C A 1318 A A 1319 A — — 1321 A —A 1322 A 1323 A A 1325 A A 1327 A 1328 A 1330 A A A 1331 A A 1332 A 1333 A A 1335 A C A 1337 A A 1338 A 1339 A A 1340 A A 1341 A 1342 A 1343 A A 1345 A 1346 A 1347 A 1348 A 1349 A 1350 A 1351 A A 1352 A A 1353 A A A 1355 A A A 1356 A 1358 A C 1360 A C 1361 A 1362 A A A 1363 A 1364 A A A 1365 A 1366 A A A 1367 A 1368 A 1370 A A 1372 A 1373 A 1374 A 1376 A 1379 A 1381 A C 1382 A A A 1383 A A A 1384 A A A 1385 A A A 1386 A A A 1387 A A A 1388 A D A 1389 A A A 1390 A A 1392 A A 1393 A A 1394 A A 1395 A 1398 A 1399 A A A 1400 A A A 1401 A 1402 A A A 1404 A C A 1406 A A A 1409 A A 1410 A A 1411 A A 1412 A 1414 A A A 1415 A A 1416 A 1417 A A A 1418 A A A 1419 A A 1420 A A 1421 A 1423 A 1424 A A 1427 A A A 1428 A A A 1429 A A A 1430 A D A 1431 A 1432 A 1434 A 1436 A A A 1438 A A A 1439 A C 1440 A 1441 A A 1442 A 1443 A 1445 A A A 1446 A 1447 A A A 1448 A A A 1449 A A A 1450 A A A 1451 A 1452 A A A 1453 A 1454 A A A 1456 A A 1457 A A 1458 A A A 1459 A A 1460 A C A 1461 A A 1464 A A A 1465 A A 1466 A A A 1467 A A A 1468 A C A 1469 A 1470 A A 1472 A A A 1473 A A A 1474 A A A 1475 A A A 1476 A 1478 A A A 1479 A A A 1480 A 1481 A A A 1482 A A A 1484 A A A 1485 A A A 1486 A A 1487 A A 1488 A A 1489 A A A 1490 A A 1491 A A A 1492 A A 1493 A A 1494 A A A 1495 A A A 1496 A A A 1497 A A A 1498 A A A 1499 A A A 1500 A A A 1501 A A A 1502 A A A 1503 A C A 1504 A A A 1505 A A A 1506 A A A 1507 A A A 1508 A C A 1509 A C A 1510 A A 1511 A 1512 A A A 1513 A 1514 A A 1515 A 1516 A A A 1517 A A 1518 A 1519 A A 1520 A 1521 A 1522 A A A 1523 A A 1524 A A A 1525 A A A 1526 A A A 1527 A A 1528 A A 1529 A A 1530 A A 1531 A A A 1532 A A A 1533 A A A 1534 A A A 1535 A A A 1536 A A A 1537 A A A 1538 A A A 1539 A A A 1540 A A A 1541 A A A 1542 A D A 1543 A A A 1544 A A A 1545 A D A 1546 A C A 1547 A A 1548 A A 1549 A D A 1550 A A A 1551 A D A 1552 A A A 1553 A A 1554 A A 1555 A A 1556 A A A 1557 A A A 1558 A C A 1559 A A A 1560 A A A 1561 A A A 1562 A A A 1563 A A A 1565 A A A 1566 A A A 1567 A A A 1568 A A A 1569 A A A 1570 A 1571 A A A 1572 A A A 1573 A A A 1574 A A A 1575 A A 1576 A D A 1577 A 1578 A A 1579 A 1580 A A A 1581 A A A 1582 A A 1583 A A 1584 A A 1585 A A A 1586 A C A 1587 A A A 1588 A A 1589 A A 1590 A A A 1594 A A — 1595 A A — 1596 A A — 1597 A A — 1598 A A — 1599 A A — 1600 A A — 1601 A A — 1602 A A A 1603 A A A 1604 A A A 1605 A C — 1606 A A — 1607 A A — 1608 A A — 1609 A A — 1610 A A — 1611 A — 1612 A A — 1613 A A — 1614 A C A 1615 A A A 1617 A A 1618 A C A 1619 A A — 1620 A A 1622 A A 1623 A C A 1624 A D A 1625 A A A 1626 A A 1627 A A A 1628 A A A 1629 A A A 1632 A A 1633 A A A 1634 A A A 1635 A A A 1636 A D A 1637 A A A 1638 A A A 1639 A A A 1640 A A A 1641 A A 1642 A A A 1643 A A 1644 A A A 1645 A A A 1646 A A A 1647 A A A 1648 A A A 1649 A A A 1650 A A A 1651 A A A 1652 A A A 1653 A A A 1654 A A A 1655 A A A 1656 A A A 1658 A 1659 A A 1660 A A — 1661 A — 1662 A A — 1663 A A — 1664 A A — 1665 A A — 1666 A A — 1667 A A — 1668 A A — 1669 A A — 1670 A A — 1671 A A — 1672 A A — 1673 A — 1674 A A — 1679 A A A 1680 A A A 1681 A A A 1682 A A — 1683 A — 1684 A A — 1685 A A — 1686 A A — 1689 A A — 1690 A A — 1691 A A — 1692 A — 1693 A A — 1694 A — 1695 A A — 1696 A A — 1697 A A — 1698 A — 1699 A A — 1700 A D — 1714 A A A 1715 A A A 1716 A A A 1717 A A A 1722 A A A 1723 A A A 1726 A A 1727 A A 1732 A A A 1733 A A A 1737 A C A 1742 A A 1743 A A 1747 A C A 1748 A A 1750 A A 1752 A A 1763 A A 1764 A A A 1765 A A A 1766 A A A 1767 A 1768 A A 1770 A — A 1772 A — A 1773 A A A 1774 A — A 1775 A — A 1776 A — A 1777 A A A 1778 A — A 1799 A A A 1800 A A A 1801 A A A 1802 A 1803 A A A 1804 A 1805 A

In Table 5, “-” means that test is not conducted. 

What is claimed is:
 1. A fluorine-containing aniline compound represented by the general formula (ST-I):

wherein R^(a) is a halogen atom, a C₁-C₆ alkyl group, a C₁-C₆ alkoxy group or a trifluoromethyl group, and each of R^(b), R^(c) and R^(d) is a hydrogen atom or a C₂-C₆ perfluoroalkyl group, provided that at least one of R^(b), R^(c) and R^(d) is not a hydrogen atom, and that R^(c) is neither a pentafluoroethyl group nor a n-heptafluoropropyl group when R^(a) is a fluorine atom and each of R^(b) and R^(d) is a hydrogen atom.
 2. A fluorine-containing aniline compound according to claim 1, wherein R^(a) is a C₁-C₆ alkyl group.
 3. A fluorine-containing aniline compound according to claim 1, wherein R^(a) is a chlorine atom or a bromine atom.
 4. A fluorine-containing aniline compound according to claim 1, wherein R^(a) is a fluorine atom, each of R^(b) and R^(d) is a hydrogen atom, and R^(c) is a heptafluoropropan-2-yl group. 